EP3774828A1 - Terpene glycoside derivatives and uses thereof - Google Patents
Terpene glycoside derivatives and uses thereofInfo
- Publication number
- EP3774828A1 EP3774828A1 EP19782928.6A EP19782928A EP3774828A1 EP 3774828 A1 EP3774828 A1 EP 3774828A1 EP 19782928 A EP19782928 A EP 19782928A EP 3774828 A1 EP3774828 A1 EP 3774828A1
- Authority
- EP
- European Patent Office
- Prior art keywords
- glucosylated
- rebaudioside
- mono
- terpene glycoside
- terpene
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Pending
Links
- 235000007586 terpenes Nutrition 0.000 title claims abstract description 193
- -1 Terpene glycoside Chemical class 0.000 title claims abstract description 184
- 229930182470 glycoside Natural products 0.000 title claims abstract description 180
- 239000000203 mixture Substances 0.000 claims abstract description 110
- 150000001875 compounds Chemical class 0.000 claims abstract description 81
- 238000000034 method Methods 0.000 claims abstract description 55
- 241000196324 Embryophyta Species 0.000 claims abstract description 17
- 244000228451 Stevia rebaudiana Species 0.000 claims abstract description 13
- 241001092459 Rubus Species 0.000 claims abstract description 9
- 235000006092 Stevia rebaudiana Nutrition 0.000 claims abstract description 9
- 239000000796 flavoring agent Substances 0.000 claims abstract description 6
- 235000019634 flavors Nutrition 0.000 claims abstract description 6
- 235000000346 sugar Nutrition 0.000 claims description 49
- 108010059892 Cellulase Proteins 0.000 claims description 35
- QSRAJVGDWKFOGU-WBXIDTKBSA-N rebaudioside c Chemical compound O[C@@H]1[C@H](O)[C@@H](O)[C@H](C)O[C@H]1O[C@@H]1[C@@H](O[C@H]2[C@@H]([C@@H](O)[C@H](O)[C@@H](CO)O2)O)[C@H](O)[C@@H](CO)O[C@H]1O[C@]1(CC[C@H]2[C@@]3(C)[C@@H]([C@](CCC3)(C)C(=O)O[C@H]3[C@@H]([C@@H](O)[C@H](O)[C@@H](CO)O3)O)CC3)C(=C)C[C@]23C1 QSRAJVGDWKFOGU-WBXIDTKBSA-N 0.000 claims description 27
- RPYRMTHVSUWHSV-CUZJHZIBSA-N rebaudioside D Chemical compound O([C@H]1[C@H](O)[C@@H](CO)O[C@H]([C@@H]1O[C@H]1[C@@H]([C@@H](O)[C@H](O)[C@@H](CO)O1)O)O[C@]12C(=C)C[C@@]3(C1)CC[C@@H]1[C@@](C)(CCC[C@]1([C@@H]3CC2)C)C(=O)O[C@H]1[C@@H]([C@@H](O)[C@H](O)[C@@H](CO)O1)O[C@H]1[C@@H]([C@@H](O)[C@H](O)[C@@H](CO)O1)O)[C@@H]1O[C@H](CO)[C@@H](O)[C@H](O)[C@H]1O RPYRMTHVSUWHSV-CUZJHZIBSA-N 0.000 claims description 25
- HELXLJCILKEWJH-NCGAPWICSA-N rebaudioside A Chemical compound O([C@H]1[C@H](O)[C@@H](CO)O[C@H]([C@@H]1O[C@H]1[C@@H]([C@@H](O)[C@H](O)[C@@H](CO)O1)O)O[C@]12C(=C)C[C@@]3(C1)CC[C@@H]1[C@@](C)(CCC[C@]1([C@@H]3CC2)C)C(=O)O[C@H]1[C@@H]([C@@H](O)[C@H](O)[C@@H](CO)O1)O)[C@@H]1O[C@H](CO)[C@@H](O)[C@H](O)[C@H]1O HELXLJCILKEWJH-NCGAPWICSA-N 0.000 claims description 21
- YWPVROCHNBYFTP-OSHKXICASA-N rubusoside Chemical compound O([C@]12C(=C)C[C@@]3(C1)CC[C@@H]1[C@@](C)(CCC[C@]1([C@@H]3CC2)C)C(=O)O[C@H]1[C@@H]([C@@H](O)[C@H](O)[C@@H](CO)O1)O)[C@@H]1O[C@H](CO)[C@@H](O)[C@H](O)[C@H]1O YWPVROCHNBYFTP-OSHKXICASA-N 0.000 claims description 19
- UEDUENGHJMELGK-HYDKPPNVSA-N Stevioside Chemical group O([C@@H]1[C@@H](O)[C@H](O)[C@@H](CO)O[C@H]1O[C@]12C(=C)C[C@@]3(C1)CC[C@@H]1[C@@](C)(CCC[C@]1([C@@H]3CC2)C)C(=O)O[C@H]1[C@@H]([C@@H](O)[C@H](O)[C@@H](CO)O1)O)[C@@H]1O[C@H](CO)[C@@H](O)[C@H](O)[C@H]1O UEDUENGHJMELGK-HYDKPPNVSA-N 0.000 claims description 17
- DRSKVOAJKLUMCL-MMUIXFKXSA-N u2n4xkx7hp Chemical compound O([C@H]1[C@H](O)[C@@H](CO)O[C@H]([C@@H]1O[C@H]1[C@@H]([C@@H](O)[C@H](O)[C@@H](CO)O1)O)O[C@]12C(=C)C[C@@]3(C1)CC[C@@H]1[C@@](C)(CCC[C@]1([C@@H]3CC2)C)C(O)=O)[C@@H]1O[C@H](CO)[C@@H](O)[C@H](O)[C@H]1O DRSKVOAJKLUMCL-MMUIXFKXSA-N 0.000 claims description 17
- CANAPGLEBDTCAF-NTIPNFSCSA-N Dulcoside A Chemical compound O[C@@H]1[C@H](O)[C@@H](O)[C@H](C)O[C@H]1O[C@H]1[C@H](O[C@]23C(C[C@]4(C2)[C@H]([C@@]2(C)[C@@H]([C@](CCC2)(C)C(=O)O[C@H]2[C@@H]([C@@H](O)[C@H](O)[C@@H](CO)O2)O)CC4)CC3)=C)O[C@H](CO)[C@@H](O)[C@@H]1O CANAPGLEBDTCAF-NTIPNFSCSA-N 0.000 claims description 16
- JLPRGBMUVNVSKP-AHUXISJXSA-M chembl2368336 Chemical compound [Na+].O([C@H]1[C@@H](O)[C@H](O)[C@H](CO)O[C@H]1O[C@]12C(=C)C[C@@]3(C1)CC[C@@H]1[C@@](C)(CCC[C@]1([C@@H]3CC2)C)C([O-])=O)[C@@H]1O[C@@H](CO)[C@@H](O)[C@H](O)[C@@H]1O JLPRGBMUVNVSKP-AHUXISJXSA-M 0.000 claims description 16
- RLLCWNUIHGPAJY-SFUUMPFESA-N rebaudioside E Chemical compound O([C@@H]1[C@@H](O)[C@H](O)[C@@H](CO)O[C@H]1O[C@]12C(=C)C[C@@]3(C1)CC[C@@H]1[C@@](C)(CCC[C@]1([C@@H]3CC2)C)C(=O)O[C@H]1[C@@H]([C@@H](O)[C@H](O)[C@@H](CO)O1)O[C@H]1[C@@H]([C@@H](O)[C@H](O)[C@@H](CO)O1)O)[C@@H]1O[C@H](CO)[C@@H](O)[C@H](O)[C@H]1O RLLCWNUIHGPAJY-SFUUMPFESA-N 0.000 claims description 16
- GSGVXNMGMKBGQU-PHESRWQRSA-N rebaudioside M Chemical compound C[C@@]12CCC[C@](C)([C@H]1CC[C@@]13CC(=C)[C@@](C1)(CC[C@@H]23)O[C@@H]1O[C@H](CO)[C@@H](O)[C@H](O[C@@H]2O[C@H](CO)[C@@H](O)[C@H](O)[C@H]2O)[C@H]1O[C@@H]1O[C@H](CO)[C@@H](O)[C@H](O)[C@H]1O)C(=O)O[C@@H]1O[C@H](CO)[C@@H](O)[C@H](O[C@@H]2O[C@H](CO)[C@@H](O)[C@H](O)[C@H]2O)[C@H]1O[C@@H]1O[C@H](CO)[C@@H](O)[C@H](O)[C@H]1O GSGVXNMGMKBGQU-PHESRWQRSA-N 0.000 claims description 16
- HYLAUKAHEAUVFE-AVBZULRRSA-N rebaudioside f Chemical compound O([C@H]1[C@H](O)[C@@H](CO)O[C@H]([C@@H]1O[C@H]1[C@@H]([C@@H](O)[C@H](O)CO1)O)O[C@]12C(=C)C[C@@]3(C1)CC[C@@H]1[C@@](C)(CCC[C@]1([C@@H]3CC2)C)C(=O)O[C@H]1[C@@H]([C@@H](O)[C@H](O)[C@@H](CO)O1)O)[C@@H]1O[C@H](CO)[C@@H](O)[C@H](O)[C@H]1O HYLAUKAHEAUVFE-AVBZULRRSA-N 0.000 claims description 16
- 229930188195 rebaudioside Natural products 0.000 claims description 13
- 235000019202 steviosides Nutrition 0.000 claims description 13
- YWPVROCHNBYFTP-UHFFFAOYSA-N Rubusoside Natural products C1CC2C3(C)CCCC(C)(C(=O)OC4C(C(O)C(O)C(CO)O4)O)C3CCC2(C2)CC(=C)C21OC1OC(CO)C(O)C(O)C1O YWPVROCHNBYFTP-UHFFFAOYSA-N 0.000 claims description 12
- 235000019605 sweet taste sensations Nutrition 0.000 claims description 12
- LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 claims description 11
- GUBGYTABKSRVRQ-CUHNMECISA-N D-Cellobiose Chemical compound O[C@@H]1[C@@H](O)[C@H](O)[C@@H](CO)O[C@H]1O[C@@H]1[C@@H](CO)OC(O)[C@H](O)[C@H]1O GUBGYTABKSRVRQ-CUHNMECISA-N 0.000 claims description 10
- 239000001512 FEMA 4601 Substances 0.000 claims description 10
- 239000001776 FEMA 4720 Substances 0.000 claims description 10
- HELXLJCILKEWJH-SEAGSNCFSA-N Rebaudioside A Natural products O=C(O[C@H]1[C@@H](O)[C@@H](O)[C@H](O)[C@@H](CO)O1)[C@@]1(C)[C@@H]2[C@](C)([C@H]3[C@@]4(CC(=C)[C@@](O[C@H]5[C@H](O[C@H]6[C@H](O)[C@@H](O)[C@H](O)[C@@H](CO)O6)[C@@H](O[C@H]6[C@H](O)[C@@H](O)[C@H](O)[C@@H](CO)O6)[C@H](O)[C@@H](CO)O5)(C4)CC3)CC2)CCC1 HELXLJCILKEWJH-SEAGSNCFSA-N 0.000 claims description 10
- OMHUCGDTACNQEX-OSHKXICASA-N Steviolbioside Natural products O([C@@H]1[C@@H](O)[C@H](O)[C@@H](CO)O[C@H]1O[C@]12C(=C)C[C@@]3(C1)CC[C@@H]1[C@@](C)(CCC[C@]1([C@@H]3CC2)C)C(O)=O)[C@@H]1O[C@H](CO)[C@@H](O)[C@H](O)[C@H]1O OMHUCGDTACNQEX-OSHKXICASA-N 0.000 claims description 10
- HELXLJCILKEWJH-UHFFFAOYSA-N entered according to Sigma 01432 Natural products C1CC2C3(C)CCCC(C)(C(=O)OC4C(C(O)C(O)C(CO)O4)O)C3CCC2(C2)CC(=C)C21OC(C1OC2C(C(O)C(O)C(CO)O2)O)OC(CO)C(O)C1OC1OC(CO)C(O)C(O)C1O HELXLJCILKEWJH-UHFFFAOYSA-N 0.000 claims description 10
- 235000019203 rebaudioside A Nutrition 0.000 claims description 10
- OHHNJQXIOPOJSC-UHFFFAOYSA-N stevioside Natural products CC1(CCCC2(C)C3(C)CCC4(CC3(CCC12C)CC4=C)OC5OC(CO)C(O)C(O)C5OC6OC(CO)C(O)C(O)C6O)C(=O)OC7OC(CO)C(O)C(O)C7O OHHNJQXIOPOJSC-UHFFFAOYSA-N 0.000 claims description 10
- 229940013618 stevioside Drugs 0.000 claims description 10
- CANAPGLEBDTCAF-QHSHOEHESA-N Dulcoside A Natural products C[C@@H]1O[C@H](O[C@@H]2[C@@H](O)[C@H](O)[C@@H](CO)O[C@H]2O[C@]34CC[C@H]5[C@]6(C)CCC[C@](C)([C@H]6CC[C@@]5(CC3=C)C4)C(=O)O[C@@H]7O[C@H](CO)[C@@H](O)[C@H](O)[C@H]7O)[C@H](O)[C@H](O)[C@H]1O CANAPGLEBDTCAF-QHSHOEHESA-N 0.000 claims description 9
- RLLCWNUIHGPAJY-RYBZXKSASA-N Rebaudioside E Natural products O=C(O[C@H]1[C@H](O[C@H]2[C@H](O)[C@@H](O)[C@@H](O)[C@@H](CO)O2)[C@@H](O)[C@@H](O)[C@H](CO)O1)[C@]1(C)[C@@H]2[C@@](C)([C@@H]3[C@@]4(CC(=C)[C@@](O[C@@H]5[C@@H](O[C@@H]6[C@@H](O)[C@H](O)[C@@H](O)[C@H](CO)O6)[C@H](O)[C@@H](O)[C@H](CO)O5)(C4)CC3)CC2)CCC1 RLLCWNUIHGPAJY-RYBZXKSASA-N 0.000 claims description 9
- QRGRAFPOLJOGRV-UHFFFAOYSA-N rebaudioside F Natural products CC12CCCC(C)(C1CCC34CC(=C)C(CCC23)(C4)OC5OC(CO)C(O)C(OC6OCC(O)C(O)C6O)C5OC7OC(CO)C(O)C(O)C7O)C(=O)OC8OC(CO)C(O)C(O)C8O QRGRAFPOLJOGRV-UHFFFAOYSA-N 0.000 claims description 9
- 150000003505 terpenes Chemical class 0.000 claims description 6
- 239000007864 aqueous solution Substances 0.000 claims description 3
- 230000002708 enhancing effect Effects 0.000 claims description 2
- 238000004519 manufacturing process Methods 0.000 claims 1
- 235000003599 food sweetener Nutrition 0.000 abstract description 6
- 239000003765 sweetening agent Substances 0.000 abstract description 6
- 241001409321 Siraitia grosvenorii Species 0.000 abstract description 2
- 235000011171 Thladiantha grosvenorii Nutrition 0.000 abstract description 2
- 235000012041 food component Nutrition 0.000 abstract description 2
- 239000005417 food ingredient Substances 0.000 abstract description 2
- 229940106157 cellulase Drugs 0.000 description 21
- 125000000188 beta-D-glucosyl group Chemical group C1([C@H](O)[C@@H](O)[C@H](O)[C@H](O1)CO)* 0.000 description 20
- 235000019640 taste Nutrition 0.000 description 19
- 125000002791 glucosyl group Chemical group C1([C@H](O)[C@@H](O)[C@H](O)[C@H](O1)CO)* 0.000 description 17
- 239000000243 solution Substances 0.000 description 14
- 239000007858 starting material Substances 0.000 description 13
- 238000006243 chemical reaction Methods 0.000 description 11
- 235000013305 food Nutrition 0.000 description 11
- 239000000284 extract Substances 0.000 description 10
- 235000013361 beverage Nutrition 0.000 description 9
- 229930006000 Sucrose Natural products 0.000 description 8
- CZMRCDWAGMRECN-UGDNZRGBSA-N Sucrose Chemical compound O[C@H]1[C@H](O)[C@@H](CO)O[C@@]1(CO)O[C@@H]1[C@H](O)[C@@H](O)[C@H](O)[C@@H](CO)O1 CZMRCDWAGMRECN-UGDNZRGBSA-N 0.000 description 8
- 239000005720 sucrose Substances 0.000 description 8
- 238000000746 purification Methods 0.000 description 7
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 6
- 235000009508 confectionery Nutrition 0.000 description 6
- 235000019533 nutritive sweetener Nutrition 0.000 description 6
- 239000011541 reaction mixture Substances 0.000 description 6
- 235000015067 sauces Nutrition 0.000 description 6
- 229930182478 glucoside Natural products 0.000 description 5
- 241000202807 Glycyrrhiza Species 0.000 description 4
- 235000001453 Glycyrrhiza echinata Nutrition 0.000 description 4
- 235000006200 Glycyrrhiza glabra Nutrition 0.000 description 4
- 235000017382 Glycyrrhiza lepidota Nutrition 0.000 description 4
- 239000002585 base Substances 0.000 description 4
- 229940010454 licorice Drugs 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- 241001465754 Metazoa Species 0.000 description 3
- 239000004383 Steviol glycoside Substances 0.000 description 3
- FYGDTMLNYKFZSV-ZWSAEMDYSA-N cellotriose Chemical compound O[C@@H]1[C@@H](O)[C@H](O)[C@@H](CO)O[C@H]1O[C@@H]1[C@@H](CO)O[C@@H](O[C@@H]2[C@H](OC(O)[C@H](O)[C@H]2O)CO)[C@H](O)[C@H]1O FYGDTMLNYKFZSV-ZWSAEMDYSA-N 0.000 description 3
- 235000013339 cereals Nutrition 0.000 description 3
- 235000019219 chocolate Nutrition 0.000 description 3
- 235000013365 dairy product Nutrition 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 239000012530 fluid Substances 0.000 description 3
- 235000011389 fruit/vegetable juice Nutrition 0.000 description 3
- 238000010438 heat treatment Methods 0.000 description 3
- 230000002779 inactivation Effects 0.000 description 3
- 238000011534 incubation Methods 0.000 description 3
- 235000013336 milk Nutrition 0.000 description 3
- 210000004080 milk Anatomy 0.000 description 3
- 235000013615 non-nutritive sweetener Nutrition 0.000 description 3
- 230000001953 sensory effect Effects 0.000 description 3
- 239000007787 solid Substances 0.000 description 3
- 235000019411 steviol glycoside Nutrition 0.000 description 3
- 229930182488 steviol glycoside Natural products 0.000 description 3
- 150000008144 steviol glycosides Chemical class 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- 101710156496 Endoglucanase A Proteins 0.000 description 2
- 108090000790 Enzymes Proteins 0.000 description 2
- 102000004190 Enzymes Human genes 0.000 description 2
- 229930091371 Fructose Natural products 0.000 description 2
- RFSUNEUAIZKAJO-ARQDHWQXSA-N Fructose Chemical compound OC[C@H]1O[C@](O)(CO)[C@@H](O)[C@@H]1O RFSUNEUAIZKAJO-ARQDHWQXSA-N 0.000 description 2
- 239000005715 Fructose Substances 0.000 description 2
- 241000124008 Mammalia Species 0.000 description 2
- 244000172730 Rubus fruticosus Species 0.000 description 2
- LUEWUZLMQUOBSB-ZLBHSGTGSA-N alpha-maltotetraose Chemical compound O[C@@H]1[C@@H](O)[C@H](O)[C@@H](CO)O[C@@H]1O[C@@H]1[C@@H](CO)O[C@H](O[C@@H]2[C@H](O[C@H](O[C@@H]3[C@H](O[C@H](O)[C@H](O)[C@H]3O)CO)[C@H](O)[C@H]2O)CO)[C@H](O)[C@H]1O LUEWUZLMQUOBSB-ZLBHSGTGSA-N 0.000 description 2
- 235000015173 baked goods and baking mixes Nutrition 0.000 description 2
- OCIBBXPLUVYKCH-FYTDUCIRSA-N beta-D-cellohexaose Chemical compound O[C@@H]1[C@@H](O)[C@H](O)[C@@H](CO)O[C@H]1O[C@@H]1[C@@H](CO)O[C@@H](O[C@@H]2[C@H](O[C@@H](O[C@@H]3[C@H](O[C@@H](O[C@@H]4[C@H](O[C@@H](O[C@@H]5[C@H](O[C@@H](O)[C@H](O)[C@H]5O)CO)[C@H](O)[C@H]4O)CO)[C@H](O)[C@H]3O)CO)[C@H](O)[C@H]2O)CO)[C@H](O)[C@H]1O OCIBBXPLUVYKCH-FYTDUCIRSA-N 0.000 description 2
- 235000019658 bitter taste Nutrition 0.000 description 2
- 238000001460 carbon-13 nuclear magnetic resonance spectrum Methods 0.000 description 2
- 108010085318 carboxymethylcellulase Proteins 0.000 description 2
- OCIBBXPLUVYKCH-UHFFFAOYSA-N cellopentanose Natural products OC1C(O)C(O)C(CO)OC1OC1C(CO)OC(OC2C(OC(OC3C(OC(OC4C(OC(OC5C(OC(O)C(O)C5O)CO)C(O)C4O)CO)C(O)C3O)CO)C(O)C2O)CO)C(O)C1O OCIBBXPLUVYKCH-UHFFFAOYSA-N 0.000 description 2
- FTNIPWXXIGNQQF-XHCCAYEESA-N cellopentaose Chemical compound O[C@@H]1[C@@H](O)[C@H](O)[C@@H](CO)O[C@H]1O[C@@H]1[C@@H](CO)O[C@@H](O[C@@H]2[C@H](O[C@@H](O[C@@H]3[C@H](O[C@@H](O[C@@H]4[C@H](OC(O)[C@H](O)[C@H]4O)CO)[C@H](O)[C@H]3O)CO)[C@H](O)[C@H]2O)CO)[C@H](O)[C@H]1O FTNIPWXXIGNQQF-XHCCAYEESA-N 0.000 description 2
- 229920002678 cellulose Polymers 0.000 description 2
- 239000001913 cellulose Substances 0.000 description 2
- 235000013409 condiments Nutrition 0.000 description 2
- 235000013399 edible fruits Nutrition 0.000 description 2
- 239000003623 enhancer Substances 0.000 description 2
- 230000002255 enzymatic effect Effects 0.000 description 2
- 229940088598 enzyme Drugs 0.000 description 2
- 238000001914 filtration Methods 0.000 description 2
- 150000002338 glycosides Chemical class 0.000 description 2
- 230000000415 inactivating effect Effects 0.000 description 2
- 239000004615 ingredient Substances 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 239000008267 milk Substances 0.000 description 2
- 230000000116 mitigating effect Effects 0.000 description 2
- 230000035807 sensation Effects 0.000 description 2
- 235000019615 sensations Nutrition 0.000 description 2
- 239000000758 substrate Substances 0.000 description 2
- 235000014101 wine Nutrition 0.000 description 2
- HTSGKJQDMSTCGS-UHFFFAOYSA-N 1,4-bis(4-chlorophenyl)-2-(4-methylphenyl)sulfonylbutane-1,4-dione Chemical compound C1=CC(C)=CC=C1S(=O)(=O)C(C(=O)C=1C=CC(Cl)=CC=1)CC(=O)C1=CC=C(Cl)C=C1 HTSGKJQDMSTCGS-UHFFFAOYSA-N 0.000 description 1
- 229920002498 Beta-glucan Polymers 0.000 description 1
- 244000056139 Brassica cretica Species 0.000 description 1
- 235000003351 Brassica cretica Nutrition 0.000 description 1
- 235000003343 Brassica rupestris Nutrition 0.000 description 1
- 241000195940 Bryophyta Species 0.000 description 1
- 235000002568 Capsicum frutescens Nutrition 0.000 description 1
- 208000024172 Cardiovascular disease Diseases 0.000 description 1
- 229920002299 Cellodextrin Polymers 0.000 description 1
- 108010084185 Cellulases Proteins 0.000 description 1
- 102000005575 Cellulases Human genes 0.000 description 1
- 241000207199 Citrus Species 0.000 description 1
- 235000016795 Cola Nutrition 0.000 description 1
- 235000011824 Cola pachycarpa Nutrition 0.000 description 1
- FKLJPTJMIBLJAV-UHFFFAOYSA-N Compound IV Chemical compound O1N=C(C)C=C1CCCCCCCOC1=CC=C(C=2OCCN=2)C=C1 FKLJPTJMIBLJAV-UHFFFAOYSA-N 0.000 description 1
- 235000003363 Cornus mas Nutrition 0.000 description 1
- 240000006766 Cornus mas Species 0.000 description 1
- 206010013911 Dysgeusia Diseases 0.000 description 1
- 239000004097 EU approved flavor enhancer Substances 0.000 description 1
- 101710156500 Endoglucanase D Proteins 0.000 description 1
- 108090000604 Hydrolases Proteins 0.000 description 1
- 102000004157 Hydrolases Human genes 0.000 description 1
- 108010093096 Immobilized Enzymes Proteins 0.000 description 1
- 235000007688 Lycopersicon esculentum Nutrition 0.000 description 1
- 235000005135 Micromeria juliana Nutrition 0.000 description 1
- 208000008589 Obesity Diseases 0.000 description 1
- 101710147478 Probable endo-beta-1,4-glucanase D Proteins 0.000 description 1
- 235000012098 RTD tea Nutrition 0.000 description 1
- 240000002114 Satureja hortensis Species 0.000 description 1
- 235000007315 Satureja hortensis Nutrition 0.000 description 1
- VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 1
- 240000003768 Solanum lycopersicum Species 0.000 description 1
- 244000185386 Thladiantha grosvenorii Species 0.000 description 1
- 241000251539 Vertebrata <Metazoa> Species 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 235000013334 alcoholic beverage Nutrition 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 235000019606 astringent taste Nutrition 0.000 description 1
- 235000008452 baby food Nutrition 0.000 description 1
- 235000013405 beer Nutrition 0.000 description 1
- 108010047754 beta-Glucosidase Proteins 0.000 description 1
- 102000006995 beta-Glucosidase Human genes 0.000 description 1
- QKSKPIVNLNLAAV-UHFFFAOYSA-N bis(2-chloroethyl) sulfide Chemical compound ClCCSCCCl QKSKPIVNLNLAAV-UHFFFAOYSA-N 0.000 description 1
- 235000008429 bread Nutrition 0.000 description 1
- 235000015496 breakfast cereal Nutrition 0.000 description 1
- 235000012970 cakes Nutrition 0.000 description 1
- 150000001720 carbohydrates Chemical class 0.000 description 1
- 235000014633 carbohydrates Nutrition 0.000 description 1
- 235000012174 carbonated soft drink Nutrition 0.000 description 1
- 238000005119 centrifugation Methods 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 229940112822 chewing gum Drugs 0.000 description 1
- 235000015218 chewing gum Nutrition 0.000 description 1
- 235000019987 cider Nutrition 0.000 description 1
- 235000020971 citrus fruits Nutrition 0.000 description 1
- 235000008504 concentrate Nutrition 0.000 description 1
- 239000012141 concentrate Substances 0.000 description 1
- 239000000470 constituent Substances 0.000 description 1
- 235000014510 cooky Nutrition 0.000 description 1
- 239000006071 cream Substances 0.000 description 1
- 230000007423 decrease Effects 0.000 description 1
- 239000008367 deionised water Substances 0.000 description 1
- 229910021641 deionized water Inorganic materials 0.000 description 1
- 230000001419 dependent effect Effects 0.000 description 1
- 206010012601 diabetes mellitus Diseases 0.000 description 1
- 229940079919 digestives enzyme preparation Drugs 0.000 description 1
- 229930004069 diterpene Natural products 0.000 description 1
- 235000012489 doughnuts Nutrition 0.000 description 1
- 238000007580 dry-mixing Methods 0.000 description 1
- 239000007938 effervescent tablet Substances 0.000 description 1
- NLFBCYMMUAKCPC-KQQUZDAGSA-N ethyl (e)-3-[3-amino-2-cyano-1-[(e)-3-ethoxy-3-oxoprop-1-enyl]sulfanyl-3-oxoprop-1-enyl]sulfanylprop-2-enoate Chemical compound CCOC(=O)\C=C\SC(=C(C#N)C(N)=O)S\C=C\C(=O)OCC NLFBCYMMUAKCPC-KQQUZDAGSA-N 0.000 description 1
- 235000013861 fat-free Nutrition 0.000 description 1
- 235000021554 flavoured beverage Nutrition 0.000 description 1
- 235000019264 food flavour enhancer Nutrition 0.000 description 1
- 238000009472 formulation Methods 0.000 description 1
- 235000015038 fortified wine Nutrition 0.000 description 1
- 235000012055 fruits and vegetables Nutrition 0.000 description 1
- 239000008103 glucose Substances 0.000 description 1
- 230000036541 health Effects 0.000 description 1
- 235000015243 ice cream Nutrition 0.000 description 1
- 238000001802 infusion Methods 0.000 description 1
- 235000014109 instant soup Nutrition 0.000 description 1
- 238000002955 isolation Methods 0.000 description 1
- 235000014058 juice drink Nutrition 0.000 description 1
- 235000008960 ketchup Nutrition 0.000 description 1
- 235000019223 lemon-lime Nutrition 0.000 description 1
- 235000014666 liquid concentrate Nutrition 0.000 description 1
- 235000021577 malt beverage Nutrition 0.000 description 1
- 235000010746 mayonnaise Nutrition 0.000 description 1
- 239000008268 mayonnaise Substances 0.000 description 1
- 208000030159 metabolic disease Diseases 0.000 description 1
- 229930189775 mogroside Natural products 0.000 description 1
- 235000011929 mousse Nutrition 0.000 description 1
- 235000010460 mustard Nutrition 0.000 description 1
- 235000008486 nectar Nutrition 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 1
- 235000020824 obesity Nutrition 0.000 description 1
- 150000002894 organic compounds Chemical class 0.000 description 1
- 238000004806 packaging method and process Methods 0.000 description 1
- 235000021485 packed food Nutrition 0.000 description 1
- 239000002245 particle Substances 0.000 description 1
- 238000009928 pasteurization Methods 0.000 description 1
- 235000014594 pastries Nutrition 0.000 description 1
- 230000008447 perception Effects 0.000 description 1
- 239000000419 plant extract Substances 0.000 description 1
- 235000008476 powdered milk Nutrition 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 238000004321 preservation Methods 0.000 description 1
- 102000004169 proteins and genes Human genes 0.000 description 1
- 108090000623 proteins and genes Proteins 0.000 description 1
- 238000000425 proton nuclear magnetic resonance spectrum Methods 0.000 description 1
- 230000005180 public health Effects 0.000 description 1
- 235000011962 puddings Nutrition 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- 235000021572 root beer Nutrition 0.000 description 1
- 235000014438 salad dressings Nutrition 0.000 description 1
- 239000000523 sample Substances 0.000 description 1
- 230000011664 signaling Effects 0.000 description 1
- 239000001632 sodium acetate Substances 0.000 description 1
- 235000017281 sodium acetate Nutrition 0.000 description 1
- BHZOKUMUHVTPBX-UHFFFAOYSA-M sodium acetic acid acetate Chemical compound [Na+].CC(O)=O.CC([O-])=O BHZOKUMUHVTPBX-UHFFFAOYSA-M 0.000 description 1
- 235000014214 soft drink Nutrition 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 238000001179 sorption measurement Methods 0.000 description 1
- 239000007921 spray Substances 0.000 description 1
- 235000020354 squash Nutrition 0.000 description 1
- 230000001954 sterilising effect Effects 0.000 description 1
- 238000004659 sterilization and disinfection Methods 0.000 description 1
- 150000008163 sugars Chemical class 0.000 description 1
- 235000020357 syrup Nutrition 0.000 description 1
- 239000006188 syrup Substances 0.000 description 1
- 235000013616 tea Nutrition 0.000 description 1
- 239000012085 test solution Substances 0.000 description 1
- 230000026683 transduction Effects 0.000 description 1
- 238000010361 transduction Methods 0.000 description 1
- 230000001960 triggered effect Effects 0.000 description 1
- 235000019583 umami taste Nutrition 0.000 description 1
- 239000003643 water by type Substances 0.000 description 1
- 235000013618 yogurt Nutrition 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
- C07H13/00—Compounds containing saccharide radicals esterified by carbonic acid or derivatives thereof, or by organic acids, e.g. phosphonic acids
- C07H13/02—Compounds containing saccharide radicals esterified by carbonic acid or derivatives thereof, or by organic acids, e.g. phosphonic acids by carboxylic acids
- C07H13/08—Compounds containing saccharide radicals esterified by carbonic acid or derivatives thereof, or by organic acids, e.g. phosphonic acids by carboxylic acids having the esterifying carboxyl radicals directly attached to carbocyclic rings
-
- A—HUMAN NECESSITIES
- A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
- A23L—FOODS, FOODSTUFFS, OR NON-ALCOHOLIC BEVERAGES, NOT COVERED BY SUBCLASSES A21D OR A23B-A23J; THEIR PREPARATION OR TREATMENT, e.g. COOKING, MODIFICATION OF NUTRITIVE QUALITIES, PHYSICAL TREATMENT; PRESERVATION OF FOODS OR FOODSTUFFS, IN GENERAL
- A23L2/00—Non-alcoholic beverages; Dry compositions or concentrates therefor; Their preparation
- A23L2/52—Adding ingredients
- A23L2/60—Sweeteners
-
- A—HUMAN NECESSITIES
- A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
- A23L—FOODS, FOODSTUFFS, OR NON-ALCOHOLIC BEVERAGES, NOT COVERED BY SUBCLASSES A21D OR A23B-A23J; THEIR PREPARATION OR TREATMENT, e.g. COOKING, MODIFICATION OF NUTRITIVE QUALITIES, PHYSICAL TREATMENT; PRESERVATION OF FOODS OR FOODSTUFFS, IN GENERAL
- A23L27/00—Spices; Flavouring agents or condiments; Artificial sweetening agents; Table salts; Dietetic salt substitutes; Preparation or treatment thereof
- A23L27/30—Artificial sweetening agents
- A23L27/33—Artificial sweetening agents containing sugars or derivatives
- A23L27/36—Terpene glycosides
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
- C07H1/00—Processes for the preparation of sugar derivatives
- C07H1/06—Separation; Purification
- C07H1/08—Separation; Purification from natural products
-
- C—CHEMISTRY; METALLURGY
- C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
- C12N—MICROORGANISMS OR ENZYMES; COMPOSITIONS THEREOF; PROPAGATING, PRESERVING, OR MAINTAINING MICROORGANISMS; MUTATION OR GENETIC ENGINEERING; CULTURE MEDIA
- C12N9/00—Enzymes; Proenzymes; Compositions thereof; Processes for preparing, activating, inhibiting, separating or purifying enzymes
- C12N9/14—Hydrolases (3)
- C12N9/24—Hydrolases (3) acting on glycosyl compounds (3.2)
- C12N9/2402—Hydrolases (3) acting on glycosyl compounds (3.2) hydrolysing O- and S- glycosyl compounds (3.2.1)
- C12N9/2405—Glucanases
- C12N9/2434—Glucanases acting on beta-1,4-glucosidic bonds
- C12N9/2437—Cellulases (3.2.1.4; 3.2.1.74; 3.2.1.91; 3.2.1.150)
-
- C—CHEMISTRY; METALLURGY
- C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
- C12P—FERMENTATION OR ENZYME-USING PROCESSES TO SYNTHESISE A DESIRED CHEMICAL COMPOUND OR COMPOSITION OR TO SEPARATE OPTICAL ISOMERS FROM A RACEMIC MIXTURE
- C12P19/00—Preparation of compounds containing saccharide radicals
- C12P19/14—Preparation of compounds containing saccharide radicals produced by the action of a carbohydrase (EC 3.2.x), e.g. by alpha-amylase, e.g. by cellulase, hemicellulase
-
- C—CHEMISTRY; METALLURGY
- C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
- C12P—FERMENTATION OR ENZYME-USING PROCESSES TO SYNTHESISE A DESIRED CHEMICAL COMPOUND OR COMPOSITION OR TO SEPARATE OPTICAL ISOMERS FROM A RACEMIC MIXTURE
- C12P19/00—Preparation of compounds containing saccharide radicals
- C12P19/44—Preparation of O-glycosides, e.g. glucosides
- C12P19/56—Preparation of O-glycosides, e.g. glucosides having an oxygen atom of the saccharide radical directly bound to a condensed ring system having three or more carbocyclic rings, e.g. daunomycin, adriamycin
-
- C—CHEMISTRY; METALLURGY
- C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
- C12Y—ENZYMES
- C12Y302/00—Hydrolases acting on glycosyl compounds, i.e. glycosylases (3.2)
- C12Y302/01—Glycosidases, i.e. enzymes hydrolysing O- and S-glycosyl compounds (3.2.1)
- C12Y302/01004—Cellulase (3.2.1.4), i.e. endo-1,4-beta-glucanase
-
- A—HUMAN NECESSITIES
- A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
- A23V—INDEXING SCHEME RELATING TO FOODS, FOODSTUFFS OR NON-ALCOHOLIC BEVERAGES AND LACTIC OR PROPIONIC ACID BACTERIA USED IN FOODSTUFFS OR FOOD PREPARATION
- A23V2002/00—Food compositions, function of food ingredients or processes for food or foodstuffs
Definitions
- the present disclosure relates generally to terpene glycosides, such as certain such compounds extracted from Stevia rebaudiana Bertoni, Rubus suavissimus, or Siraitia grosvenorii.
- the disclosure also provides for the use of such compounds as food ingredients, flavors, and sweeteners, and related methods.
- the disclosure also provides ingestible compositions comprising such compounds, as well as processes for extracting such compounds selectively from certain plant sources.
- the taste system provides sensory information about the chemical composition of the external world.
- Taste transduction is one of the more sophisticated forms of chemically triggered sensation in animals. Signaling of taste is found throughout the animal kingdom, from simple metazoans to the most complex of vertebrates. Mammals are believed to have five basic taste modalities: sweet, bitter, sour, salty, and umami.
- Sweetness is the taste most commonly perceived when eating foods rich in sugars. Mammals generally perceive sweetness to be a pleasurable sensation, except in excess.
- Caloric sweeteners such as sucrose and fructose, are the prototypical examples of sweet substances. Although a variety of no-calorie and low-calorie substitutes exist, these caloric sweeteners are still the predominant means by which comestible products induce the perception of sweetness upon consumption.
- Metabolic disorders and related conditions such as obesity, diabetes, and others
- Caloric sweeteners are a key contributor to this trend, as they are included in various packaged food and beverage products to make them more palatable to consumers.
- no-calorie or low-calorie substitutes can be used in foods and beverages in place of sucrose or fructose. Even so, these compounds impart sweetness differently from caloric sweeteners, and a number of consumers fail to view them as suitable alternatives.
- such compounds may be difficult to incorporate into certain products. In some instances, they may be used as partial replacements for caloric sweeteners, but their mere presence can cause many consumers to perceive an unpleasant astringency. Therefore, lower-calorie sweeteners still face certain challenges to their adoption.
- Terpene glycosides such as steviol glycosides from Stevia (Stevia rebaudiana Bertoni) extracts, rubusoside from blackberry leaf ( Rubus suavissimus ) extracts, and mogrosides from monk fruit ( Siraitis grosvenorii ) extracts, are natural low-calorie sweeteners. But these products, like many other low-calorie sugar alternatives, have negative taste attributes, such as bitterness, lingering aftertaste, or licorice flavor. Transglucosylation provides a way of mitigating some of these negative taste attributes. But many of the presently disclosed glucosylated low-calorie sweeteners continue to exhibit negative taste attributes that prevent their widespread adoption. Thus, there is a continuing need to develop glucosylated products and transglucosylation methods that can provide more effective mitigation of negative taste attributes.
- the disclosure provides methods of making a glucosylated terpene glycoside, the method comprising: (a) providing an aqueous composition comprising a b-glucosyl sugar compound, a terpene glycoside, and a cellulase enzyme; and (b) reacting the b-glucosyl sugar compound with the terpene glycoside in the presence of the cellulase enzyme to form a glucosylated terpene glycoside having a terpene glycosidyl moiety and one or more b-glucosyl sugar moieties, wherein the glucosylated terpene glycoside has one b-1,4 glucosidic bond between the terpene glycoside moiety and one of the one or more b-glucosyl sugar moieties.
- the reacting comprises incubating the aqueous composition.
- the aqueous composition is an aqueous solution.
- the disclosure provides methods of reducing an unpleasant taste of a terpene glycoside, the method comprising: (a) providing an aqueous composition comprising an b-glucosyl sugar compound, a terpene glycoside, and a cellulase enzyme; and (b) reacting the b-glucosyl sugar compound with the terpene glycoside in the presence of the cellulase enzyme to form a glucosylated terpene glycoside having a terpene glycosidyl moiety and one or more b-glucosyl sugar moieties, wherein the glucosylated terpene glycoside has one b-1,4 glucosidic bond between the terpene glycoside moiety and one of the one or more b-glucosyl sugar moieties.
- the reacting comprises incubating the aqueous composition.
- the aqueous composition is an aqueous solution.
- the terpene glycoside is stevioside, rebaudioside A, rebaudioside B, rebaudioside C, rebaudioside D, rebaudioside E, rebaudioside F, rebaudioside G, rebaudioside M, dulcoside A, steviolbioside, rubusoside, terpene glycosides found in Stevia rebaudiana Bertoni plants, terpene glycosides found in Rubus suavissimus plants, terpene glycosides found in Siraitis grosvenorii plants, or any mixtures thereof.
- the beta-glucosyl sugar compound is cellobiose.
- the glucosylated terpene glycoside is mono b-1,4 glucosylated stevioside, mono b-1,4 glucosylated rebaudioside A, mono b-1,4 glucosylated rebaudioside B, mono b-1,4 glucosylated rebaudioside C, mono b-1,4 glucosylated rebaudioside D, mono b-1,4 glucosylated rebaudioside E, mono b-1,4 glucosylated rebaudioside F mono b-1,4 glucosylated rebaudioside G, mono b-1,4 glucosylated rebaudioside M, mono b-1,4 glucosylated dulcoside A,
- the disclosure provides a compound of formula I:
- the disclosure provides a compound of formula II:
- the disclosure provides a compound of formula III:
- the disclosure provides a compound of formula IV:
- the disclosure provides a composition comprising at least one glucosylated terpene glycoside selected from the group consisting of: mono b-1,4 glucosylated stevioside, mono b-1,4 glucosylated rebaudioside A, mono b-1,4 glucosylated rebaudioside B, mono b-1,4 glucosylated rebaudioside C, mono b-1,4 glucosylated rebaudioside D, mono b-1,4 glucosylated rebaudioside E, mono b-1,4 glucosylated rebaudioside F, mono b-1,4 glucosylated rebaudioside G, mono b-1,4 glucosylated rebaudioside M, mono b-1,4 glucosylated dulcoside A, mono b-1,4 glucosylated
- the at one glucosylated terpene glycoside is selected from the group consisting of: mono b-1,4 cellobiosylated stevioside, mono b-1,4 cellobiosylated rebaudioside A, mono b-1,4 cellobiosylated rebaudioside B, mono b-1,4 cellobiosylated rebaudioside C, mono b-1,4 cellobiosylated rebaudioside D, mono b-1,4 cellobiosylated rebaudioside E, mono b-1,4 cellobiosylated rebaudioside F, mono b-1,4 cellobiosylated rebaudioside G, mono b-1,4 cellobiosylated rebaudioside M, mono b-1,4 cellobiosylated dulcoside A, mono b-1,
- the glucosylated terpene glycoside is a compound of the third aspect, or a compound of the fourth aspect, or a compound of the fifth aspect, or a compound of the sixth aspect.
- the glucosylated terpene glycosides in the composition confer, enhance, improve, or modify a sweet taste of a flavored article.
- the terpene glycosides are present in the composition in an amount effective to confer, enhance, improve, or modify the sweet taste of the composition.
- the composition is a flavored article.
- the composition is not a naturally occurring composition.
- the disclosure provides uses of any of the compounds of the third through the sixth aspects, or any compositions of the seventh aspect to modify the flavor of a composition, such as an ingestible composition.
- the use comprises enhancing the sweetness of an ingestible composition.
- the use comprises reducing the bitterness or reducing a lingering licorice taste of an ingestible composition.
- the composition comprises a sweetener, such as a non-caloric or caloric sweetener.
- FIG. 1 shows an HPFC chromatogram of the product enzymatically generated by cellulase with Rubusoside (Rubu) and cellobiose as substrates.
- Rubu Rubusoside
- FIG. 2 shows A NMR spectrum for a composition comprising a mixture of the compound of formula I and the compound of formula II.
- FIG. 3 shows A 13 C NMR spectrum for a composition comprising a mixture of the compound of formula I and the compound of formula II.
- the disclosure provides methods of making a glucosylated terpene glycoside, the method comprising: (a) providing an aqueous composition comprising a b-glucosyl sugar compound, a terpene glycoside, and a cellulase enzyme; and (b) reacting the b-glucosyl sugar compound with the terpene glycoside in the presence of the cellulase enzyme to form a glucosylated terpene glycoside having a terpene glycosidyl moiety and one or more b-glucosyl sugar moieties, wherein the glucosylated terpene glycoside has one b-1,4 glucosidic bond between the terpene glycoside moiety and one of the one or more b-glucosyl sugar moieties.
- the reacting comprises incubating the aqueous composition.
- the disclosure provides methods of reducing an unpleasant taste of a terpene glycoside, the method comprising: (a) providing an aqueous composition comprising an b-glucosyl sugar compound, a terpene glycoside, and a cellulase enzyme; and (b) reacting the b-glucosyl sugar compound with the terpene glycoside in the presence of the cellulase enzyme to form a glucosylated terpene glycoside having a terpene glycosidyl moiety and one or more b-glucosyl sugar moieties, wherein the glucosylated terpene glycoside has one b-1,4 glucosidic bond between the terpene glycoside moiety and one of the one or more b-glucosyl sugar moieties.
- the reacting comprises incubating the aqueous composition.
- the terpene glycoside is stevioside, rebaudioside A, rebaudioside B, rebaudioside C, rebaudioside D, rebaudioside E, rebaudioside F, rebaudioside G, rebaudioside M, dulcoside A, steviolbioside, rubusoside, terpene glycosides found in Stevia rebaudiana Bertoni plants, terpene glycosides found in Rubus suavissimus plants, terpene glycosides found in Siraitis grosvenorii plants, or mixtures thereof.
- the starting material (e.g., the terpene glycoside) for the enzymatic process is an extract of a Stevia rebaudiana Bertoni plant, an extract of a Rubus suavissimus plant, or an extract of a Siraitis grosvenorii plant.
- the plant extracts contain one or more than one terpene glycosides.
- Stevia rebaudiana Bertoni produces a number of diterpene glycosides, including stevioside, rebaudioside A, rebaudioside B, rebaudioside C, rebaudioside D, rebaudioside E, rebaudioside F, rebaudioside G, rebaudioside M, dulcoside A, and steviolbioside.
- rubusoside is obtained from blackberry leaves ( Rubus suavissimus) containing substantially a single terpene glycoside called mbusoside.
- mbusoside is found in low amounts in stevia leaves.
- mbusoside is found in extracts of stevia leaves ( Stevia rebaudiana Bertoni).
- the starting material for the enzymatic process e.g., the terpene glycoside
- the terpene glycoside is a terpene glycoside purified from either an extract of a Stevia
- the terpene glycoside starting material is selected from the group consisting of: stevioside, rebaudioside A, rebaudioside B, rebaudioside C,
- rebaudioside D rebaudioside E
- rebaudioside F rebaudioside G
- rebaudioside M dulcoside A
- steviolbioside mbusoside
- mixtures thereof rebaudioside D, rebaudioside E, rebaudioside F, rebaudioside G, rebaudioside M, dulcoside A, steviolbioside, mbusoside, and mixtures thereof.
- the terpene glycoside starting material is selected from the group consisting of: stevioside, rebaudioside A, rebaudioside B, rebaudioside C, and mbusoside.
- the terpene glycoside starting material is the starting material disclosed in U.S. Patent No. 8,257,948.
- the terpene glycoside starting material is the starting material disclosed in PCT Publication No. WO 2017/089444.
- the terpene glycoside starting material is the starting material disclosed in PCT Publication No. WO 2013/019050.
- the terpene glycoside starting material is the starting material disclosed in European Patent Application Publication No. 3003058.
- glycoside refers to an organic compound to which one or more sugar units are covalently bound at one or more sites of the chemical structure.
- the aqueous composition comprises deionized water.
- the aqueous composition comprises sodium acetate.
- the aqueous composition is a solution.
- the aqueous composition can have any suitable pH.
- the pH of the aqueous composition ranges from pH 4.0 to pH 7.0.
- the pH of the aqueous composition ranges from pH 4.0 to pH 6.0.
- the pH of the aqueous composition ranges from pH 4.0 to pH 5.0.
- the pH of the aqueous composition ranges from pH 5.0 to pH 7.0.
- the pH of the aqueous composition ranges from pH 6.0 to pH 7.0.
- the pH of the aqueous composition is pH 4.0, or 4.1, or 4.2, or 4.3, or 4.4, or 4.5, or 4.6, or 4.7, or 4.8, or 4.9, or 5.0, or 5.1, or 5.2, or 5.3, or 5.4, or 5.5, or 5.6, or 5.7, or 5.8, or 5.9, or 6.0, or 6.1, or 6.2, or 6.3, or 6.4, or 6.5, or 6.6, or 6.7, or 6.8, or 6.9, or 7.0.
- the pH of the aqueous composition is pH of about 5.0.
- the terpene glycoside can be added to the aqueous composition in any suitable concentration.
- the terpene glucoside is added to the aqueous composition at a concentration of from 0.005 g/mL to 0.5 g/mL.
- the terpene glucoside is added to the aqueous composition at a concentration of from 0.05 mL to 0.25 g/mL.
- the terpene glucoside is added to the aqueous composition at a concentration of from 0.1 g/mL to 0.2 g/mL.
- any suitable beta-glucosyl sugar compound can be used.
- the beta-glucosyl sugar compound is a reducing sugar comprising two b-glucose molecules linked by a b-1,4 bond.
- the beta-glucosyl sugar compound is selected from the group consisting of: cellobiose, cellotriose, cellotetraose, cellopentaose, and cellohexaose.
- the beta-glucosyl sugar compound is a reducing sugar comprising two b-glucose molecules linked by a b-1,4 bond.
- the beta-glucosyl sugar compound is selected from the group consisting of: cellobiose, cellotriose, cellotetraose, cellopentaose, and cellohexaose.
- the beta-glucosyl sugar compound is selected from the group consisting of: cellobiose, cellotriose, cellotetraose, cellopentaose, and cellohexao
- beta-glucosyl sugar compound is selected from the group consisting of: cellotriose, cellotetraose, cellopentaose, and cellohexaose. In some embodiments, the
- beta-glucosyl sugar compound is cellobiose. In some embodiments, the beta-glucosyl sugar compound is a cellodextrin. In some embodiments, the beta-glucosyl sugar compound is a cellulose, or a derivative thereof. In some embodiments, the beta-glucosyl sugar compound is cellobiose.
- the beta-glucosyl sugar compound can be added to the aqueous composition in any suitable concentration.
- the concentration of the beta-glucosyl sugar compound in the aqueous composition ranges from 10% to 40% (wt/wt), or from 20% to 30% (wt/wt).
- the concentration of the beta-glucosyl sugar compound in the aqueous composition ranges from 0.005 g/mL to 0.5 g/mL.
- the concentration of the beta-glucosyl sugar compound in the aqueous composition is about 0.2 g/mL.
- the terpene glycoside can be present in the aqueous composition at any suitable ratio relative to the beta-glucosyl sugar compound.
- the ratio (wt/wt) of the terpene glycoside to the beta-glucosyl sugar compound in the aqueous composition ranges from 100: 1 to 1: 100.
- the ratio (wt/wt) of the terpene glycoside to the beta-glucosyl sugar compound in the aqueous composition ranges from 10: 1 to 1: 10.
- the ratio (wt/wt) of the terpene glycoside to the beta-glucosyl sugar compound in the aqueous composition is about 1 : 1.
- cellulase is present in the aqueous composition and performs a transglucosylation reaction, thereby generating glucosylated terpene glycoside having a single glucosyl residue linked to the terpene glycoside via a b-1,4 glucosidic bond.
- the transglucosidase performs a transglucosylation reaction, thereby generating a glucosylated terpene glycoside having one or more glucose residues covalently attached to the terpene glycoside via a b-1,4 glucosidic bond.
- the number of glucose residues that are added to the terpene glycoside is controlled by parameters such as, for example, the time of the reaction, the temperature of the reaction, the concentration of the terpene glycoside, the concentration of the beta-glucosyl sugar compound, and the like.
- the cellulase performs the transglucosylation reaction, using cellobiose as a substrate, thereby generating a glucosylated terpene glycoside wherein two glucose units are added to the terpene glycoside via a b-1,4 glucosidic bond.
- the cellulase performs a transglucosylation reaction, thereby generating glucosylated terpene glycoside having a single cellobiosyl residue linked to the terpene glycoside via a b-1,4 glucosidic bond.
- the transglucosidase performs a transglucosylation reaction, thereby generating a glucosylated terpene glycoside having one or more cellobiosyl residues covalently attached to the terpene glycoside via a b-1,4 glucosidic bond.
- the number of cellobiosyl residues that are added to the terpene glycoside is controlled by parameters such as, for example, the time of the reaction, the temperature of the reaction, the concentration of the terpene glycoside, the concentration of the beta-glucosyl sugar compound, and the like.
- the cellulase is in a form of cell-free culture broth, concentrated liquid cell-free culture broth, spray dried or freeze dried cell-free culture broth, or high purity protein. Free and immobilized enzyme preparations may also be used.
- cellulase include endo-l,4-beta-D-glucanase (beta-l,4-glucanase, beta-l,4-endoglucan hydrolase,
- endoglucanase D l,4-(l,3,l,4)-beta-D-glucan 4-glucanohydrolase
- carboxymethyl cellulase CMCase
- avicelase carboxymethyl cellulase
- celludextrinase cellulase A
- cellulosin AP cellulosin AP
- alkali cellulase cellulase A 3
- pancellase SS pancellase
- the cellulase can be added at any suitable concentration.
- the cellulase is added to the aqueous composition at an concentration ranging from 0.2 to 0.4 units per gram of beta-glucosyl sugar compound.
- the cellulase is added to the aqueous composition at a concentration ranging from 2 mg/mL to 200 mg/mL.
- the cellulase is added to the aqueous composition at c concentration of about 40 mg/mL.
- the terpene glycoside can be used at any suitable concentration relative to the cellulase enzyme.
- the ratio (w/w) of the terpene glycoside to the cellulase enzyme in the aqueous composition ranges from 100: 1 to 1 : 100, or from 10:1 to 1 : 10. In some embodiments, the ratio (w/w) of the terpene glycoside to the cellulase enzyme in the aqueous composition is about 1 : 1.
- the ratio of the amount of cellulase enzyme in wt% relative to the amount of terpene glycoside ranges from 0.1% to 100%, or from 1% to 50%, or from 10% to 20%.
- the mixture containing the cellulase is incubated, e.g., for a time and temperature sufficient to generate the glucosylated terpene glycoside.
- the glucosylated terpene glycoside is a glucosylated terpene glycoside having a single glucosyl residue linked to the terpene glycoside via a b-1,4 glucosidic bond.
- the glucosylated terpene glycoside is a glucosylated terpene glycoside having a single cellobiosyl residue linked to the terpene glycoside via a b-1,4 glucosidic bond.
- the mixture containing the cellulase is incubated for a time and temperature sufficient to generate the glucosylated terpene glycoside having a single cellobiosyl residue linked to the terpene glycoside via a b-1,4 glucosidic bond.
- any suitable temperature can be used for the incubation.
- the temperature ranges from 30 to 90 °C, or from 70 to 90 °C. In some embodiments, the temperature is about 60 °C. In some embodiments, the temperature is about 37 °C.
- the incubation can be carried out for any suitable length of time. In some embodiments,
- the time sufficient is 24 hours or greater. In some embodiments, the time sufficient is 24 hours, or less. In some embodiments, the time sufficient is 24 hours, or 23 hours, or 22 hours, or 21 hours, or 20 hours, or 19 hours, or 18 hours, or 17 hours, or 16 hours, or 15 hours, or 14 hours, or 13 hours, or 12 hours, or 11 hours, or 10 hours, or 9 hours, or 8 hours, or 7 hours, or 6 hours, or 5 hours, or 4 hours, or 3 hours, or 2 hours, or 1 hour. In some embodiments, the time sufficient is about 24 hours.
- the mixture containing the glucosylated terpene glycoside may treated further.
- Such further treatment may include, for example, an inactivation step or a purification step, wherein the glucosylated terpene glycoside is isolated or purified.
- the glucosylated terpene glycoside is a glucosylated terpene glycoside having a single glucosyl residue linked to the terpene glycoside via a b-1,4 glucosidic bond.
- the glucosylated terpene glycoside is a glucosylated terpene glycoside having a single cellobiosyl residue linked to the terpene glycoside via a b-1,4 glucosidic bond.
- Non-limiting examples of the purification step include enrichment, isolation, or purification of the glucosylated terpene glycoside, or the removal of solids from the reaction mixture.
- the glucosylated terpene glycoside is a glucosylated terpene glycoside having a single glucosyl residue linked to the terpene glycoside via a b-1,4 glucosidic bond.
- the glucosylated terpene glycoside is a glucosylated terpene glycoside having a single cellobiosyl residue linked to the terpene glycoside via a b-1,4 glucosidic bond.
- the further treatment includes inactivating the cellulase.
- the cellulase is inactivated by the application of heat.
- the cellulase is inactivated by heating the reaction mixture to a temperature sufficient to inactivate the cellulase. In some such embodiments, the temperature sufficient is 100 °C.
- U.S. Patent 8,257,948 discloses some examples of purification steps that may be utilized in some aspects of the present disclosure to isolate or purify the glucosylated terpene glycoside.
- PCT Publication No. WO 2017/089444 discloses other examples of purification steps that may be utilized in some aspects of the present disclosure to isolate or purify the glucosylated terpene glucoside.
- PCT Publication No. WO 2013/019050 discloses other examples of purification steps that may be utilized in some aspects of the present disclosure to isolate or the glucosylated terpene glycoside.
- European Patent Application Publication No. 3003058 discloses other examples of purification steps that may be utilized in some aspects of the present disclosure to isolate or purify the glucosylated terpene glycoside.
- U.S. Patent 8,257,948 discloses some examples of inactivation steps that may be utilized in some aspects of the present disclosure.
- PCT Publication No. WO 2017/089444 discloses other examples of inactivation steps that may be utilized in some aspects of the present disclosure.
- the glucosylated terpene glycoside is selected from the group consisting of: mono b-1,4 glucosylated stevioside, mono b-1,4 glucosylated rebaudioside A, mono b-1,4 glucosylated rebaudioside B, mono b-1,4 glucosylated rebaudioside C, mono b-1,4 glucosylated rebaudioside D, mono b-1,4 glucosylated rebaudioside E, mono b-1,4 glucosylated rebaudioside F, mono b-1,4 glucosylated rebaudioside G, mono b-1,4 glucosylated rebaudioside M, mono b-1,4 glucosylated dulcoside A, mono b-1,4 glucosylated steviolbioside, mono b-1,4 glucosylated rubusoside, and mixtures thereof.
- the glucosylated terpene glycoside is selected from the group consisting of: di b-1,4 glucosylated stevioside, di b-1,4 glucosylated rebaudioside A, di b-1,4 glucosylated rebaudioside B, di b-1,4 glucosylated rebaudioside C, di b-1,4 glucosylated rebaudioside D, di b-1,4 glucosylated rebaudioside E, di b-1,4 glucosylated rebaudioside F, di b-1,4 glucosylated rebaudioside G, di b-1,4 glucosylated rebaudioside M, di b-1,4 glucosylated dulcoside A, di b-1,4 glucosylated steviolbioside, di b-1,4 glucosylated rubusoside, and mixtures thereof.
- the glucosylated terpene glycoside is selected from the group consisting of: mono b-1,4 cellobiosylated stevioside, mono b-1,4 cellobiosylated
- rebaudioside A mono b-1,4 cellobiosylated rebaudioside B, mono b-1,4 cellobiosylated rebaudioside C, mono b-1,4 cellobiosylated rebaudioside D, mono b-1,4 cellobiosylated rebaudioside E, mono b-1,4 cellobiosylated rebaudioside F, mono b-1,4 cellobiosylated rebaudioside G, mono b-1,4 cellobiosylated rebaudioside M, mono b-1,4 cellobiosylated dulcoside A, mono b-1,4 cellobiosylated steviolbioside, and mono b-1,4 cellobiosylated rubusoside.
- the disclosure provides a compound of formula I:
- the disclosure provides a compound of formula II:
- the disclosure provides a compound of formula III:
- the disclosure provides a compound of formula IV:
- compositions comprising at least one glucosylated terpene glycoside selected from the group consisting of: mono b-1,4 glucosylated stevioside, mono b-1,4 glucosylated rebaudioside A, mono b-1,4 glucosylated rebaudioside B, mono b-1,4 glucosylated rebaudioside C, mono b-1,4 glucosylated rebaudioside D, mono b-1,4 glucosylated rebaudioside E, mono b-1,4 glucosylated rebaudioside F, mono b-1,4 glucosylated rebaudioside M, mono b-1,4 glucosylated dulcoside A, mono b-1,4 glucosylated steviolbioside
- the composition comprises at least one glucosylated terpene glycoside selected from the group consisting of: the compound of formula I, the compound of formula II, the compound of formula III, and the compound of formula IV.
- the composition comprises at least one glucosylated terpene glycoside having a single glucosyl residue linked to the terpene glycoside via a b-1,4 glucosidic bond selected from the group consisting of: the compound of formula I and the compound of formula II.
- the composition comprises at least one glucosylated terpene glycoside having a single cellobiosylated residue linked to the terpene glycoside via a b-1,4 glucosidic bond selected from the group consisting of: the compound of formula III and the compound of formula IV.
- the one glucosylated terpene glycoside described herein may be used as sweetness enhancers, flavor enhancers, taste maskers, or sweeteners in various flavored articles.
- the glucosylated terpene glycoside is a glucosylated terpene glycoside having a single glucosyl residue linked to the terpene glycoside via a b-1,4 glucosidic bond.
- the glucosylated terpene glycoside is a glucosylated terpene glycoside having a single cellobiosyl residue linked to the terpene glycoside via a b-1,4 glucosidic bond.
- the disclosure provides the use of at least one glucosylated terpene glycoside of the foregoing aspects and embodiments to confer, enhance, improve, or modify a sweet taste of a flavored article.
- the glucosylated terpene glycoside is a glucosylated terpene glycoside having a single glucosyl residue linked to the terpene glycoside via a b-1,4 glucosidic bond.
- the glucosylated terpene glycoside is a glucosylated terpene glycoside having a single cellobiosyl residue linked to the terpene glycoside via a b-1,4 glucosidic bond.
- the disclosure provides the use of at least one glucosylated terpene glycoside according to some aspects presented herein to mask a lingering taste of a flavored article.
- the glucosylated terpene glycoside is a glucosylated terpene glycoside having a single glucosyl residue linked to the terpene glycoside via a b-1,4 glucosidic bond.
- the glucosylated terpene glycoside is a glucosylated terpene glycoside having a single cellobiosyl residue linked to the terpene glycoside via a b-1,4 glucosidic bond.
- the disclosure provides a method, wherein the method confers, enhances, improves, or modifies a sweet taste of a flavored article, wherein the method comprises adding at least one glucosylated terpene glycoside having a single glucosyl residue linked to the terpene glycoside via a b-1,4 glucosidic bond according to some aspects presented herein to the flavored article, in an amount effective to confer, enhance, improve, or modify the sweet taste of the flavored article.
- the disclosure provides a method, wherein the method masks a lingering taste of a flavored article, wherein the method comprises adding the glucosylated terpene glycoside having a single glucosyl residue linked to the terpene glycoside via a b-1,4 glucosidic bond according to some aspects presented herein to the flavored article, in an amount effective to mask the lingering taste of a flavored article.
- the disclosure provides a method, wherein the method confers, enhances, improves, or modifies a sweet taste of a flavored article, wherein the method comprises adding at least one glucosylated terpene glycoside having a single cellobiosyl residue linked to the terpene glycoside via a b-1,4 glucosidic bond according to some aspects presented herein to the flavored article, in an amount effective to confer, enhance, improve, or modify the sweet taste of the flavored article.
- the disclosure provides a method, wherein the method masks a lingering taste of a flavored article, wherein the method comprises adding the glucosylated terpene glycoside having a single cellobiosyl residue linked to the terpene glycoside via a b-1,4 glucosidic bond according to some aspects presented herein to the flavored article, in an amount effective to mask the lingering taste of a flavored article.
- the amount effective to confer, enhance, improve, or modify the sweet taste of the flavored article is about 40 ppm, such as from 30 ppm to 50 ppm, or from 20 ppm to 60 ppm, or from 10 ppm to 70 ppm. In some embodiments, the amount effective to confer, enhance, improve, or modify the sweet taste of the flavored article is less than 40 ppm. In some aspects, the amount effective to confer, enhance, improve, or modify the sweet taste of the flavored article is greater than 40 ppm. In some embodiments, the amount effective to confer, enhance, improve, or modify the sweet taste of the flavored article is from 0 and 1000 ppm.
- the disclosure provides flavored articles that comprise: the least one glucosylated terpene glycoside (of the foregoing aspects and embodiments); and a foodstuff base, wherein the glucosylated terpene glycoside is selected from the group consisting of: a glucosylated terpene glycoside having a single glucosyl residue linked to the terpene glycoside via a b-1,4 glucosidic bond, and a glucosylated terpene glycoside having a single cellobiosyl residue linked to the terpene glycoside via a b-1,4 glucosidic bond.
- Suitable foodstuffs e.g. foods or beverages are also provided herein.
- “foodstuff base” means an edible product, e.g. a food or a beverage. Therefore, a flavored article provided herein comprises the functional formulation, as well as optionally additional benefit agents, corresponding to a desired edible product, e.g., a savory cube, and a flavor effective amount of the least one glucosylated terpene glycoside described herein.
- the glucosylated terpene glycoside is a glucosylated terpene glycoside having a single glucosyl residue linked to the terpene glycoside via a b-1,4 glucosidic bond.
- the glucosylated terpene glycoside is a glucosylated terpene glycoside having a single cellobiosyl residue linked to the terpene glycoside via a b-1,4 glucosidic bond.
- compositions and methods provided herein have use in food or beverage products.
- the dry particles may easily be added thereto by dry-mixing.
- Typical food products are selected from the group consisting of an instant soup or sauce, a breakfast cereal, a powdered milk, a baby food, a powdered drink, a powdered chocolate drink, a spread, a powdered cereal drink, a chewing gum, an effervescent tablet, a cereal bar, and a chocolate bar.
- the powdered foods or drinks may be intended to be consumed after reconstitution of the product with water, milk and/or a juice, or another aqueous liquid.
- the food product may be selected from the group consisting of condiments, baked goods, powdery food, bakery filings and fluid dairy products.
- Condiments include, without limitation, ketchup, mayonnaise, salad dressing, Worcestershire sauce, fruit-flavored sauce, chocolate sauce, tomato sauce, chili sauce, and mustard.
- Baked goods include, without limitation, cakes, cookies, pastries, breads, donuts and the like.
- Bakery fillings include, without limitation, low or neutral pH fillings, high, medium or low solids fillings, fruit or milk based (pudding type or mousse type) fillings, hot or cold make-up fillings and nonfat to full-fat fillings.
- Fluid dairy products include, without limitation, non-frozen, partially frozen and frozen fluid dairy products such as, for example, milks, ice creams, sorbets and yogurts.
- Beverage products include, without limitation, carbonated soft drinks, including cola, lemon- lime, root beer, heavy citrus ("dew type"), fruit flavored and cream sodas; powdered soft drinks, as well as liquid concentrates such as fountain syrups and cordials; coffee and coffee - based drinks, coffee substitutes and cereal-based beverages; teas, including dry mix products as well as ready -to-drink teas (herbal and tealeaf based); fruit and vegetable juices and juice flavored beverages as well as juice drinks, nectars, concentrates, punches and "ades";
- sweetened and flavored waters both carbonated and still; sport/energy/health drinks;
- alcoholic beverages plus alcohol-free and other low- alcohol products including beer and malt beverages, cider, and wines (still, sparkling, fortified wines and wine coolers); other beverages processed with heating (infusions, pasteurization, ultra-high temperature, ohmic heating or commercial aseptic sterilization) and hot- filled packaging; and cold-filled products made through filtration or other preservation techniques.
- the proportions in which the least one glucosylated terpene glycoside described herein can be incorporated into the various aforementioned articles or compositions vary within a wide range of values. These values are dependent on the nature of the article to be flavored and on the desired organoleptic effect as well as the nature of the co-ingredients in a given base when the compounds according to the invention are mixed with flavoring co ingredients, solvents or additives commonly used in the art.
- concentrations are in the order of about 0.0001 wt% to 1 wt%, or even more, of the least one glucosylated terpene glycoside described herein based on the weight of the consumer product into which they are incorporated. Concentrations lower than these, such as in the order of 0.001 wt% to 0.5 wt% by weight, can be used when the least one glucosylated terpene glycoside described herein are incorporated into flavored articles, percentage being relative to the weight of the article.
- the resulting reaction mixture was analyzed by UPLC-UV, and a mixture containing glucosylated terpene glycosides having a single glucosyl residue linked to the terpene glycoside via a b-1,4 glucosidic bond was identified (See FIG. 1).
- the identified mixture was purified via a prep-LC.
- the compounds within the mixture were identified as compounds I and II, at a ratio of 2: 1.
- FIG. 2 shows A 1 H NMR spectrum for a composition comprising a mixture of the compound of formula I and the compound of formula II.
- FIG. 3 shows A 13 C NMR spectrum for a composition comprising a mixture of the compound of formula I and the compound of formula II.
- Example 2 Sensory Properties of a Composition Comprising Compounds I and II
- a composition comprising a mixture of the compound of formula I and the compound of formula II at a ratio (w/w) of 2:1 was generated according to the methods described in Example 1.
- the composition was dissolved in either a (i) 4% w/w sucrose solution, or (ii) a 0.02% w/w 95% steviol glycoside solution.
- a panel of 25 trained people evaluated the test solutions for taste properties (sweet, licorice and sweet lingering) on a scale of -5 to 5 (-5 denoted no effect and 5 denoted extremely strong effect, 0 being the intensity of a reference water solution containing either (i) 4% w/w sucrose solution, or (ii) a 0.02% w/w 95% steviol glycoside solution.) The results are shown in the table below.
- composition comprising Compounds I and II at a ratio of 2: 1 significantly enhanced the sweet intensity of the 4% w/w sucrose solution (at 99.9% of confidence level), with and without a nose-clip.
- Example 3 Sensory Properties of a Composition Comprising the at Least One Mono P-l,4-glucosylated Terpene Glycosides Presented Herein
- a composition comprising the at least one glucosylated terpene glucosides may be generated according to the methods described in Example 1.
- the composition may be dissolved in either (i) water, or (ii) a 4% w/w sucrose solution, or (iii) 7% (w/w) inverted sugar plus 0.15% citric acid (w/w) solution wherein the final concentration of the
- composition in solution may range from 0 to 1000 ppm.
- Corresponding control solutions of either (i) 1.5%, or (ii) 4% w/w sucrose, or (iii) 7% (w/w) inverted sugar plus 0.15% citric acid (w/w) solution will also be generated.
- a panel of 10 experts will evaluate the difference between solution of the test composition and the sucrose solutions, using the 3 -Alternative Forced Choice (3 -AFC) or sweetness intensity scale method. All samples will be tested in blind in a random order.
- 3 -AFC 3 -Alternative Forced Choice
Landscapes
- Chemical & Material Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Health & Medical Sciences (AREA)
- Genetics & Genomics (AREA)
- Biochemistry (AREA)
- General Health & Medical Sciences (AREA)
- Zoology (AREA)
- Wood Science & Technology (AREA)
- Biotechnology (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Food Science & Technology (AREA)
- Polymers & Plastics (AREA)
- Nutrition Science (AREA)
- Molecular Biology (AREA)
- General Engineering & Computer Science (AREA)
- Microbiology (AREA)
- General Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Proteomics, Peptides & Aminoacids (AREA)
- Biomedical Technology (AREA)
- Medicinal Chemistry (AREA)
- Seasonings (AREA)
- Preparation Of Compounds By Using Micro-Organisms (AREA)
- Saccharide Compounds (AREA)
Abstract
The present disclosure relates generally to terpene glycosides, such as certain such compounds extracted from Stevia rebaudiana Bertoni, Rubus suavissimus, or Siraitia
grosvenorii. The disclosure also provides for the use of such compounds as food ingredients, flavors, and sweeteners, and related methods. The disclosure also provides ingestible compositions comprising such compounds, as well as processes for extracting such compounds selectively from certain plant sources.
Description
TERPENE GLYCOSIDE DERIVATIVES AND USES THEREOF
CROSS-REFERENCE TO RELATED APPLICATIONS
The present application claims the benefit of priority of PCT Application No.
PCT/CN2018/108629, filed September 29, 2018, which is hereby incorporated by reference as though set forth herein in its entirety.
TECHNICAL FIELD
The present disclosure relates generally to terpene glycosides, such as certain such compounds extracted from Stevia rebaudiana Bertoni, Rubus suavissimus, or Siraitia grosvenorii. The disclosure also provides for the use of such compounds as food ingredients, flavors, and sweeteners, and related methods. The disclosure also provides ingestible compositions comprising such compounds, as well as processes for extracting such compounds selectively from certain plant sources.
DESCRIPTION OF RELATED ART
The taste system provides sensory information about the chemical composition of the external world. Taste transduction is one of the more sophisticated forms of chemically triggered sensation in animals. Signaling of taste is found throughout the animal kingdom, from simple metazoans to the most complex of vertebrates. Mammals are believed to have five basic taste modalities: sweet, bitter, sour, salty, and umami.
Sweetness is the taste most commonly perceived when eating foods rich in sugars. Mammals generally perceive sweetness to be a pleasurable sensation, except in excess. Caloric sweeteners, such as sucrose and fructose, are the prototypical examples of sweet substances. Although a variety of no-calorie and low-calorie substitutes exist, these caloric sweeteners are still the predominant means by which comestible products induce the perception of sweetness upon consumption.
Metabolic disorders and related conditions, such as obesity, diabetes, and
cardiovascular disease, are major public health concerns throughout the world. And their prevalence is increasing at alarming rates in almost every developed country. Caloric sweeteners are a key contributor to this trend, as they are included in various packaged food and beverage products to make them more palatable to consumers. In many cases, no-calorie or low-calorie substitutes can be used in foods and beverages in place of sucrose or fructose. Even so, these compounds impart sweetness differently from caloric sweeteners, and a
number of consumers fail to view them as suitable alternatives. Moreover, such compounds may be difficult to incorporate into certain products. In some instances, they may be used as partial replacements for caloric sweeteners, but their mere presence can cause many consumers to perceive an unpleasant astringency. Therefore, lower-calorie sweeteners still face certain challenges to their adoption.
Terpene glycosides, such as steviol glycosides from Stevia (Stevia rebaudiana Bertoni) extracts, rubusoside from blackberry leaf ( Rubus suavissimus ) extracts, and mogrosides from monk fruit ( Siraitis grosvenorii ) extracts, are natural low-calorie sweeteners. But these products, like many other low-calorie sugar alternatives, have negative taste attributes, such as bitterness, lingering aftertaste, or licorice flavor. Transglucosylation provides a way of mitigating some of these negative taste attributes. But many of the presently disclosed glucosylated low-calorie sweeteners continue to exhibit negative taste attributes that prevent their widespread adoption. Thus, there is a continuing need to develop glucosylated products and transglucosylation methods that can provide more effective mitigation of negative taste attributes.
SUMMARY
In a first aspect, the disclosure provides methods of making a glucosylated terpene glycoside, the method comprising: (a) providing an aqueous composition comprising a b-glucosyl sugar compound, a terpene glycoside, and a cellulase enzyme; and (b) reacting the b-glucosyl sugar compound with the terpene glycoside in the presence of the cellulase enzyme to form a glucosylated terpene glycoside having a terpene glycosidyl moiety and one or more b-glucosyl sugar moieties, wherein the glucosylated terpene glycoside has one b-1,4 glucosidic bond between the terpene glycoside moiety and one of the one or more b-glucosyl sugar moieties. In some embodiments, the reacting comprises incubating the aqueous composition. In some embodiments, the aqueous composition is an aqueous solution. In some embodiments, the b-glucosyl sugar compound is cellobiose.
In a second aspect, the disclosure provides methods of reducing an unpleasant taste of a terpene glycoside, the method comprising: (a) providing an aqueous composition comprising an b-glucosyl sugar compound, a terpene glycoside, and a cellulase enzyme; and (b) reacting the b-glucosyl sugar compound with the terpene glycoside in the presence of the cellulase enzyme to form a glucosylated terpene glycoside having a terpene glycosidyl moiety and one or more b-glucosyl sugar moieties, wherein the glucosylated terpene glycoside has one b-1,4 glucosidic bond between the terpene glycoside moiety and one of the
one or more b-glucosyl sugar moieties. In some embodiments, the reacting comprises incubating the aqueous composition. In some embodiments, the aqueous composition is an aqueous solution. In some embodiments, the b-glucosyl sugar compound is cellobiose.
In some embodiments of the first or second aspects, the terpene glycoside is stevioside, rebaudioside A, rebaudioside B, rebaudioside C, rebaudioside D, rebaudioside E, rebaudioside F, rebaudioside G, rebaudioside M, dulcoside A, steviolbioside, rubusoside, terpene glycosides found in Stevia rebaudiana Bertoni plants, terpene glycosides found in Rubus suavissimus plants, terpene glycosides found in Siraitis grosvenorii plants, or any mixtures thereof.
In some embodiments of the first or second aspects, the beta-glucosyl sugar compound is cellobiose.
In some embodiments of the first or second aspects, the glucosylated terpene glycoside is mono b-1,4 glucosylated stevioside, mono b-1,4 glucosylated rebaudioside A, mono b-1,4 glucosylated rebaudioside B, mono b-1,4 glucosylated rebaudioside C, mono b-1,4 glucosylated rebaudioside D, mono b-1,4 glucosylated rebaudioside E, mono b-1,4 glucosylated rebaudioside F mono b-1,4 glucosylated rebaudioside G, mono b-1,4 glucosylated rebaudioside M, mono b-1,4 glucosylated dulcoside A,
mono b-1,4 glucosylated steviolbioside, mono b-1,4 glucosylated rubusoside, or any mixtures thereof.
In a third aspect, the disclosure provides a compound of formula I:
In a fourth aspect, the disclosure provides a compound of formula II:
In a fifth aspect, the disclosure provides a compound of formula III:
In a sixth aspect, the disclosure provides a compound of formula IV:
In a seventh aspect, the disclosure provides a composition comprising at least one glucosylated terpene glycoside selected from the group consisting of: mono b-1,4 glucosylated stevioside, mono b-1,4 glucosylated rebaudioside A, mono b-1,4 glucosylated rebaudioside B, mono b-1,4 glucosylated rebaudioside C, mono b-1,4 glucosylated rebaudioside D, mono b-1,4 glucosylated rebaudioside E, mono b-1,4 glucosylated rebaudioside F, mono b-1,4 glucosylated rebaudioside G, mono b-1,4 glucosylated rebaudioside M, mono b-1,4 glucosylated dulcoside A, mono b-1,4 glucosylated
steviolbioside, and mono b-1,4 glucosylated rubusoside. In some further embodiments, the at one glucosylated terpene glycoside is selected from the group consisting of: mono b-1,4 cellobiosylated stevioside, mono b-1,4 cellobiosylated rebaudioside A, mono b-1,4 cellobiosylated rebaudioside B, mono b-1,4 cellobiosylated rebaudioside C, mono b-1,4 cellobiosylated rebaudioside D, mono b-1,4 cellobiosylated rebaudioside E, mono b-1,4 cellobiosylated rebaudioside F, mono b-1,4 cellobiosylated rebaudioside G, mono b-1,4 cellobiosylated rebaudioside M, mono b-1,4 cellobiosylated dulcoside A, mono b-1,4 cellobiosylated steviolbioside, and mono b-1,4 cellobiosylated rubusoside. In some embodiments thereof, the glucosylated terpene glycoside is a compound of the third aspect, or a compound of the fourth aspect, or a compound of the fifth aspect, or a compound of the sixth aspect. In some further embodiments of any of the foregoing embodiments, the
glucosylated terpene glycosides in the composition confer, enhance, improve, or modify a sweet taste of a flavored article. In some such embodiments, the terpene glycosides are present in the composition in an amount effective to confer, enhance, improve, or modify the sweet taste of the composition. In some embodiments, the composition is a flavored article.
In some embodiments, the composition is not a naturally occurring composition.
In an eighth aspect, the disclosure provides uses of any of the compounds of the third through the sixth aspects, or any compositions of the seventh aspect to modify the flavor of a composition, such as an ingestible composition. In some further embodiments, the use comprises enhancing the sweetness of an ingestible composition. In some other
embodiments, the use comprises reducing the bitterness or reducing a lingering licorice taste of an ingestible composition. In some embodiments thereof, the composition comprises a sweetener, such as a non-caloric or caloric sweetener.
BRIEF DESCRIPTION OF DRAWINGS
The following drawings are provided for purposes of illustrating various embodiments of the compositions and methods disclosed herein. The drawings are provided for illustrative purposes only, and are not intended to describe any preferred compositions or preferred methods, or to serve as a source of any limitations on the scope of the claimed inventions.
FIG. 1 shows an HPFC chromatogram of the product enzymatically generated by cellulase with Rubusoside (Rubu) and cellobiose as substrates.
FIG. 2 shows A NMR spectrum for a composition comprising a mixture of the compound of formula I and the compound of formula II.
FIG. 3 shows A 13C NMR spectrum for a composition comprising a mixture of the compound of formula I and the compound of formula II.
DETAIFED DESCRIPTION
In the following description, reference is made to specific embodiments which may be practiced, which is shown by way of illustration. These embodiments are described in detail to enable those skilled in the art to practice the invention described herein, and it is to be understood that other embodiments may be utilized and that logical changes may be made without departing from the scope of the aspects presented herein. The following description of example embodiments is, therefore, not to be taken in a limited sense, and the scope of the various aspects presented herein is defined by the appended claims.
Methods
In certain aspects, the disclosure provides methods of making a glucosylated terpene glycoside, the method comprising: (a) providing an aqueous composition comprising a b-glucosyl sugar compound, a terpene glycoside, and a cellulase enzyme; and (b) reacting the b-glucosyl sugar compound with the terpene glycoside in the presence of the cellulase enzyme to form a glucosylated terpene glycoside having a terpene glycosidyl moiety and one or more b-glucosyl sugar moieties, wherein the glucosylated terpene glycoside has one b-1,4 glucosidic bond between the terpene glycoside moiety and one of the one or more b-glucosyl sugar moieties. In some embodiments, the reacting comprises incubating the aqueous composition.
In certain related aspects, the disclosure provides methods of reducing an unpleasant taste of a terpene glycoside, the method comprising: (a) providing an aqueous composition comprising an b-glucosyl sugar compound, a terpene glycoside, and a cellulase enzyme; and (b) reacting the b-glucosyl sugar compound with the terpene glycoside in the presence of the cellulase enzyme to form a glucosylated terpene glycoside having a terpene glycosidyl moiety and one or more b-glucosyl sugar moieties, wherein the glucosylated terpene glycoside has one b-1,4 glucosidic bond between the terpene glycoside moiety and one of the one or more b-glucosyl sugar moieties. In some embodiments, the reacting comprises incubating the aqueous composition.
In some embodiments of any of the foregoing aspects and embodiments, the terpene glycoside is stevioside, rebaudioside A, rebaudioside B, rebaudioside C, rebaudioside D, rebaudioside E, rebaudioside F, rebaudioside G, rebaudioside M, dulcoside A, steviolbioside, rubusoside, terpene glycosides found in Stevia rebaudiana Bertoni plants, terpene glycosides found in Rubus suavissimus plants, terpene glycosides found in Siraitis grosvenorii plants, or mixtures thereof.
In some further embodiments, the starting material (e.g., the terpene glycoside) for the enzymatic process is an extract of a Stevia rebaudiana Bertoni plant, an extract of a Rubus suavissimus plant, or an extract of a Siraitis grosvenorii plant. In some such embodiments, the plant extracts contain one or more than one terpene glycosides.
In one non-limiting example, Stevia rebaudiana Bertoni, produces a number of diterpene glycosides, including stevioside, rebaudioside A, rebaudioside B, rebaudioside C, rebaudioside D, rebaudioside E, rebaudioside F, rebaudioside G, rebaudioside M, dulcoside A, and steviolbioside. In another non-limiting example, rubusoside is obtained from blackberry
leaves ( Rubus suavissimus) containing substantially a single terpene glycoside called mbusoside. In some other non-limiting examples, mbusoside is found in low amounts in stevia leaves. In some further such non-limiting examples, mbusoside is found in extracts of stevia leaves ( Stevia rebaudiana Bertoni).
In some embodiments, the starting material for the enzymatic process (e.g., the terpene glycoside) is a terpene glycoside purified from either an extract of a Stevia
rebaudiana Bertoni plant, an extract of a Rubus suavissimus plant, or an extract of a Siraitis grosvenorii plant.
In some embodiments, the terpene glycoside starting material is selected from the group consisting of: stevioside, rebaudioside A, rebaudioside B, rebaudioside C,
rebaudioside D, rebaudioside E, rebaudioside F, rebaudioside G, rebaudioside M, dulcoside A, steviolbioside, mbusoside, and mixtures thereof.
In some further embodiments, the terpene glycoside starting material is selected from the group consisting of: stevioside, rebaudioside A, rebaudioside B, rebaudioside C, and mbusoside.
In some embodiments, the terpene glycoside starting material is the starting material disclosed in U.S. Patent No. 8,257,948.
In some embodiments, the terpene glycoside starting material is the starting material disclosed in PCT Publication No. WO 2017/089444.
In some embodiments, the terpene glycoside starting material is the starting material disclosed in PCT Publication No. WO 2013/019050.
In some embodiments, the terpene glycoside starting material is the starting material disclosed in European Patent Application Publication No. 3003058.
As used herein, the term“glycoside” refers to an organic compound to which one or more sugar units are covalently bound at one or more sites of the chemical structure.
In some embodiments, the aqueous composition comprises deionized water.
Alternatively, in some embodiments, the aqueous composition comprises sodium acetate. In some embodiments of any of the foregoing embodiments, the aqueous composition is a solution.
The aqueous composition can have any suitable pH. In some embodiments, the pH of the aqueous composition ranges from pH 4.0 to pH 7.0. In some embodiments, the pH of the aqueous composition ranges from pH 4.0 to pH 6.0. In some embodiments, the pH of the aqueous composition ranges from pH 4.0 to pH 5.0. In some embodiments, the pH of the aqueous composition ranges from pH 5.0 to pH 7.0. In some embodiments, the pH of the
aqueous composition ranges from pH 6.0 to pH 7.0. In some embodiments, the pH of the aqueous composition is pH 4.0, or 4.1, or 4.2, or 4.3, or 4.4, or 4.5, or 4.6, or 4.7, or 4.8, or 4.9, or 5.0, or 5.1, or 5.2, or 5.3, or 5.4, or 5.5, or 5.6, or 5.7, or 5.8, or 5.9, or 6.0, or 6.1, or 6.2, or 6.3, or 6.4, or 6.5, or 6.6, or 6.7, or 6.8, or 6.9, or 7.0. In some such embodiments, the pH of the aqueous composition is pH of about 5.0.
In the methods disclosed herein, the terpene glycoside can be added to the aqueous composition in any suitable concentration. In some embodiments, the terpene glucoside is added to the aqueous composition at a concentration of from 0.005 g/mL to 0.5 g/mL. In some embodiments, the terpene glucoside is added to the aqueous composition at a concentration of from 0.05 mL to 0.25 g/mL. In some embodiments, the terpene glucoside is added to the aqueous composition at a concentration of from 0.1 g/mL to 0.2 g/mL.
In the methods disclosed herein, any suitable beta-glucosyl sugar compound can be used. In some embodiments, the beta-glucosyl sugar compound is a reducing sugar comprising two b-glucose molecules linked by a b-1,4 bond. In some embodiments, the beta-glucosyl sugar compound is selected from the group consisting of: cellobiose, cellotriose, cellotetraose, cellopentaose, and cellohexaose. In some embodiments, the
beta-glucosyl sugar compound is selected from the group consisting of: cellotriose, cellotetraose, cellopentaose, and cellohexaose. In some embodiments, the
beta-glucosyl sugar compound is cellobiose. In some embodiments, the beta-glucosyl sugar compound is a cellodextrin. In some embodiments, the beta-glucosyl sugar compound is a cellulose, or a derivative thereof. In some embodiments, the beta-glucosyl sugar compound is cellobiose.
In the methods disclosed herein, the beta-glucosyl sugar compound can be added to the aqueous composition in any suitable concentration. In some embodiments, the concentration of the beta-glucosyl sugar compound in the aqueous composition ranges from 10% to 40% (wt/wt), or from 20% to 30% (wt/wt). In some embodiments, the concentration of the beta-glucosyl sugar compound in the aqueous composition ranges from 0.005 g/mL to 0.5 g/mL. In some embodiments, the concentration of the beta-glucosyl sugar compound in the aqueous composition is about 0.2 g/mL.
In the methods disclosed herein, the terpene glycoside can be present in the aqueous composition at any suitable ratio relative to the beta-glucosyl sugar compound. In some embodiments, the ratio (wt/wt) of the terpene glycoside to the beta-glucosyl sugar compound in the aqueous composition ranges from 100: 1 to 1: 100. In some embodiments, the ratio (wt/wt) of the terpene glycoside to the beta-glucosyl sugar compound in the aqueous
composition ranges from 10: 1 to 1: 10. In some embodiments, the ratio (wt/wt) of the terpene glycoside to the beta-glucosyl sugar compound in the aqueous composition is about 1 : 1.
In some embodiments, cellulase is present in the aqueous composition and performs a transglucosylation reaction, thereby generating glucosylated terpene glycoside having a single glucosyl residue linked to the terpene glycoside via a b-1,4 glucosidic bond. In some embodiments, the transglucosidase performs a transglucosylation reaction, thereby generating a glucosylated terpene glycoside having one or more glucose residues covalently attached to the terpene glycoside via a b-1,4 glucosidic bond. In some embodiments, the number of glucose residues that are added to the terpene glycoside is controlled by parameters such as, for example, the time of the reaction, the temperature of the reaction, the concentration of the terpene glycoside, the concentration of the beta-glucosyl sugar compound, and the like.
In some embodiments, the cellulase performs the transglucosylation reaction, using cellobiose as a substrate, thereby generating a glucosylated terpene glycoside wherein two glucose units are added to the terpene glycoside via a b-1,4 glucosidic bond. In some embodiments, the cellulase performs a transglucosylation reaction, thereby generating glucosylated terpene glycoside having a single cellobiosyl residue linked to the terpene glycoside via a b-1,4 glucosidic bond. In some embodiments, the transglucosidase performs a transglucosylation reaction, thereby generating a glucosylated terpene glycoside having one or more cellobiosyl residues covalently attached to the terpene glycoside via a b-1,4 glucosidic bond. In some embodiments, the number of cellobiosyl residues that are added to the terpene glycoside is controlled by parameters such as, for example, the time of the reaction, the temperature of the reaction, the concentration of the terpene glycoside, the concentration of the beta-glucosyl sugar compound, and the like.
In some embodiments, the cellulase is in a form of cell-free culture broth, concentrated liquid cell-free culture broth, spray dried or freeze dried cell-free culture broth, or high purity protein. Free and immobilized enzyme preparations may also be used.
Any suitable cellulase can be used. As used herein, the term“cellulase” include endo-l,4-beta-D-glucanase (beta-l,4-glucanase, beta-l,4-endoglucan hydrolase,
endoglucanase D, l,4-(l,3,l,4)-beta-D-glucan 4-glucanohydrolase), carboxymethyl cellulase (CMCase), avicelase, celludextrinase, cellulase A, cellulosin AP, alkali cellulase, cellulase A 3, 9.5 cellulase, beta-glucosidase, cellulose l,4-beta-cellobiosidase, and pancellase SS.
The cellulase can be added at any suitable concentration. In some embodiments, the cellulase is added to the aqueous composition at an concentration ranging from 0.2 to 0.4 units per gram of beta-glucosyl sugar compound. In some embodiments, the cellulase is
added to the aqueous composition at a concentration ranging from 2 mg/mL to 200 mg/mL.
In some embodiments, the cellulase is added to the aqueous composition at c concentration of about 40 mg/mL.
In the methods disclosed herein, the terpene glycoside can be used at any suitable concentration relative to the cellulase enzyme. In some embodiments, the ratio (w/w) of the terpene glycoside to the cellulase enzyme in the aqueous composition ranges from 100: 1 to 1 : 100, or from 10:1 to 1 : 10. In some embodiments, the ratio (w/w) of the terpene glycoside to the cellulase enzyme in the aqueous composition is about 1 : 1.
In some embodiments, the ratio of the amount of cellulase enzyme in wt% relative to the amount of terpene glycoside ranges from 0.1% to 100%, or from 1% to 50%, or from 10% to 20%.
In some embodiments, the mixture containing the cellulase is incubated, e.g., for a time and temperature sufficient to generate the glucosylated terpene glycoside. In some embodiments, the glucosylated terpene glycoside is a glucosylated terpene glycoside having a single glucosyl residue linked to the terpene glycoside via a b-1,4 glucosidic bond.
Alternatively, in some embodiments, the glucosylated terpene glycoside is a glucosylated terpene glycoside having a single cellobiosyl residue linked to the terpene glycoside via a b-1,4 glucosidic bond. In some embodiments, the mixture containing the cellulase is incubated for a time and temperature sufficient to generate the glucosylated terpene glycoside having a single cellobiosyl residue linked to the terpene glycoside via a b-1,4 glucosidic bond.
Any suitable temperature can be used for the incubation. In some embodiments, the temperature ranges from 30 to 90 °C, or from 70 to 90 °C. In some embodiments, the temperature is about 60 °C. In some embodiments, the temperature is about 37 °C.
The incubation can be carried out for any suitable length of time. In some
embodiments, the time sufficient is 24 hours or greater. In some embodiments, the time sufficient is 24 hours, or less. In some embodiments, the time sufficient is 24 hours, or 23 hours, or 22 hours, or 21 hours, or 20 hours, or 19 hours, or 18 hours, or 17 hours, or 16 hours, or 15 hours, or 14 hours, or 13 hours, or 12 hours, or 11 hours, or 10 hours, or 9 hours, or 8 hours, or 7 hours, or 6 hours, or 5 hours, or 4 hours, or 3 hours, or 2 hours, or 1 hour. In some embodiments, the time sufficient is about 24 hours.
In some embodiments, after the incubation step, the mixture containing the glucosylated terpene glycoside may treated further. Such further treatment may include, for example, an inactivation step or a purification step, wherein the glucosylated terpene
glycoside is isolated or purified. In some aspects, the glucosylated terpene glycoside is a glucosylated terpene glycoside having a single glucosyl residue linked to the terpene glycoside via a b-1,4 glucosidic bond. Alternatively, in some aspects, the glucosylated terpene glycoside is a glucosylated terpene glycoside having a single cellobiosyl residue linked to the terpene glycoside via a b-1,4 glucosidic bond.
Non-limiting examples of the purification step include enrichment, isolation, or purification of the glucosylated terpene glycoside, or the removal of solids from the reaction mixture. In some embodiments, the glucosylated terpene glycoside is a glucosylated terpene glycoside having a single glucosyl residue linked to the terpene glycoside via a b-1,4 glucosidic bond. Alternatively, in some embodiments, the glucosylated terpene glycoside is a glucosylated terpene glycoside having a single cellobiosyl residue linked to the terpene glycoside via a b-1,4 glucosidic bond.
In some embodiments, solids are removed from the reaction mixture by means such as filtration, centrifugation, or other techniques known to those skilled in the art. In some embodiments, carbohydrates are removed from the mixture using adsorption resins, precipitation, or other techniques known to those skilled in the art. In some embodiments, the further treatment includes inactivating the cellulase. In one such example, the cellulase is inactivated by the application of heat. In some embodiments, the cellulase is inactivated by heating the reaction mixture to a temperature sufficient to inactivate the cellulase. In some such embodiments, the temperature sufficient is 100 °C.
U.S. Patent 8,257,948 discloses some examples of purification steps that may be utilized in some aspects of the present disclosure to isolate or purify the glucosylated terpene glycoside.
PCT Publication No. WO 2017/089444 discloses other examples of purification steps that may be utilized in some aspects of the present disclosure to isolate or purify the glucosylated terpene glucoside.
PCT Publication No. WO 2013/019050 discloses other examples of purification steps that may be utilized in some aspects of the present disclosure to isolate or the glucosylated terpene glycoside.
European Patent Application Publication No. 3003058 discloses other examples of purification steps that may be utilized in some aspects of the present disclosure to isolate or purify the glucosylated terpene glycoside.
U.S. Patent 8,257,948 discloses some examples of inactivation steps that may be utilized in some aspects of the present disclosure.
PCT Publication No. WO 2017/089444 discloses other examples of inactivation steps that may be utilized in some aspects of the present disclosure.
Glucosylated Terpene Glycosides
In some embodiments, the glucosylated terpene glycoside is selected from the group consisting of: mono b-1,4 glucosylated stevioside, mono b-1,4 glucosylated rebaudioside A, mono b-1,4 glucosylated rebaudioside B, mono b-1,4 glucosylated rebaudioside C, mono b-1,4 glucosylated rebaudioside D, mono b-1,4 glucosylated rebaudioside E, mono b-1,4 glucosylated rebaudioside F, mono b-1,4 glucosylated rebaudioside G, mono b-1,4 glucosylated rebaudioside M, mono b-1,4 glucosylated dulcoside A, mono b-1,4 glucosylated steviolbioside, mono b-1,4 glucosylated rubusoside, and mixtures thereof.
In some embodiments, the glucosylated terpene glycoside is selected from the group consisting of: di b-1,4 glucosylated stevioside, di b-1,4 glucosylated rebaudioside A, di b-1,4 glucosylated rebaudioside B, di b-1,4 glucosylated rebaudioside C, di b-1,4 glucosylated rebaudioside D, di b-1,4 glucosylated rebaudioside E, di b-1,4 glucosylated rebaudioside F, di b-1,4 glucosylated rebaudioside G, di b-1,4 glucosylated rebaudioside M, di b-1,4 glucosylated dulcoside A, di b-1,4 glucosylated steviolbioside, di b-1,4 glucosylated rubusoside, and mixtures thereof.
In some embodiments, the glucosylated terpene glycoside is selected from the group consisting of: mono b-1,4 cellobiosylated stevioside, mono b-1,4 cellobiosylated
rebaudioside A, mono b-1,4 cellobiosylated rebaudioside B, mono b-1,4 cellobiosylated rebaudioside C, mono b-1,4 cellobiosylated rebaudioside D, mono b-1,4 cellobiosylated rebaudioside E, mono b-1,4 cellobiosylated rebaudioside F, mono b-1,4 cellobiosylated rebaudioside G, mono b-1,4 cellobiosylated rebaudioside M, mono b-1,4 cellobiosylated dulcoside A, mono b-1,4 cellobiosylated steviolbioside, and mono b-1,4 cellobiosylated rubusoside.
In certain aspects, the disclosure provides a compound of formula I:
In certain aspects, the disclosure provides a compound of formula II:
In certain aspects, the disclosure provides a compound of formula III:
In certain aspects, the disclosure provides a compound of formula IV:
As used herein, the foregoing compounds of formulas I to IV can also be referred to as“Compound I,”“Compound II,”“Compound III,” and“Compound IV,” respectively.
In certain aspects, the disclosure provides compositions comprising at least one glucosylated terpene glycoside selected from the group consisting of: mono b-1,4 glucosylated stevioside, mono b-1,4 glucosylated rebaudioside A, mono b-1,4 glucosylated rebaudioside B, mono b-1,4 glucosylated rebaudioside C, mono b-1,4 glucosylated rebaudioside D, mono b-1,4 glucosylated rebaudioside E, mono b-1,4 glucosylated rebaudioside F, mono b-1,4 glucosylated rebaudioside M, mono b-1,4 glucosylated dulcoside A, mono b-1,4 glucosylated steviolbioside, mono b-1,4 glucosylated rubusoside, di b-1,4 glucosylated stevioside, di b-1,4 glucosylated rebaudioside A, di b-1,4 glucosylated rebaudioside B, di b-1,4 glucosylated rebaudioside C, di b-1,4 glucosylated rebaudioside D, di b-1,4 glucosylated rebaudioside E, di b-1,4 glucosylated rebaudioside F, di b-1,4 glucosylated rebaudioside M, di b-1,4 glucosylated dulcoside A, di b-1,4 glucosylated steviolbioside, di b-1,4 glucosylated rubusoside, mono b-1,4 cellobiosylated stevioside, mono b-1,4 cellobiosylated rebaudioside A, mono b-1,4 cellobiosylated rebaudioside B, mono b-1,4 cellobiosylated rebaudioside C, mono b-1,4 cellobiosylated rebaudioside D, mono b-1,4 cellobiosylated rebaudioside E, mono b-1,4 cellobiosylated rebaudioside F, mono b-1,4 cellobiosylated rebaudioside M, mono b-1,4 cellobiosylated dulcoside A, mono b-1,4 cellobiosylated steviolbioside, and mono b-1,4 cellobiosylated rubusoside.
In some embodiments, the composition comprises at least one glucosylated terpene glycoside selected from the group consisting of: the compound of formula I, the compound of formula II, the compound of formula III, and the compound of formula IV.
In some embodiments, the composition comprises at least one glucosylated terpene glycoside having a single glucosyl residue linked to the terpene glycoside via a b-1,4 glucosidic bond selected from the group consisting of: the compound of formula I and the compound of formula II.
In some embodiments, the composition comprises at least one glucosylated terpene glycoside having a single cellobiosylated residue linked to the terpene glycoside via a b-1,4 glucosidic bond selected from the group consisting of: the compound of formula III and the compound of formula IV.
Sweeteners or Sweetness Enhancers
The one glucosylated terpene glycoside described herein may be used as sweetness enhancers, flavor enhancers, taste maskers, or sweeteners in various flavored articles. In some embodiments, the glucosylated terpene glycoside is a glucosylated terpene glycoside having a single glucosyl residue linked to the terpene glycoside via a b-1,4 glucosidic bond.
Alternatively, in some embodiments, the glucosylated terpene glycoside is a glucosylated terpene glycoside having a single cellobiosyl residue linked to the terpene glycoside via a b-1,4 glucosidic bond.
In certain aspects, the disclosure provides the use of at least one glucosylated terpene glycoside of the foregoing aspects and embodiments to confer, enhance, improve, or modify a sweet taste of a flavored article. In some embodiments, the glucosylated terpene glycoside is a glucosylated terpene glycoside having a single glucosyl residue linked to the terpene glycoside via a b-1,4 glucosidic bond. Alternatively, in some embodiments, the glucosylated terpene glycoside is a glucosylated terpene glycoside having a single cellobiosyl residue linked to the terpene glycoside via a b-1,4 glucosidic bond.
In certain aspects, the disclosure provides the use of at least one glucosylated terpene glycoside according to some aspects presented herein to mask a lingering taste of a flavored article. In some embodiments, the glucosylated terpene glycoside is a glucosylated terpene glycoside having a single glucosyl residue linked to the terpene glycoside via a b-1,4 glucosidic bond. Alternatively, in some embodiments, the glucosylated terpene glycoside is a glucosylated terpene glycoside having a single cellobiosyl residue linked to the terpene glycoside via a b-1,4 glucosidic bond.
In certain aspects, the disclosure provides a method, wherein the method confers, enhances, improves, or modifies a sweet taste of a flavored article, wherein the method comprises adding at least one glucosylated terpene glycoside having a single glucosyl residue linked to the terpene glycoside via a b-1,4 glucosidic bond according to some aspects presented herein to the flavored article, in an amount effective to confer, enhance, improve, or modify the sweet taste of the flavored article.
In certain aspects, the disclosure provides a method, wherein the method masks a lingering taste of a flavored article, wherein the method comprises adding the glucosylated terpene glycoside having a single glucosyl residue linked to the terpene glycoside via a b-1,4 glucosidic bond according to some aspects presented herein to the flavored article, in an amount effective to mask the lingering taste of a flavored article.
In certain aspects, the disclosure provides a method, wherein the method confers, enhances, improves, or modifies a sweet taste of a flavored article, wherein the method comprises adding at least one glucosylated terpene glycoside having a single cellobiosyl residue linked to the terpene glycoside via a b-1,4 glucosidic bond according to some aspects presented herein to the flavored article, in an amount effective to confer, enhance, improve, or modify the sweet taste of the flavored article.
In certain aspects, the disclosure provides a method, wherein the method masks a lingering taste of a flavored article, wherein the method comprises adding the glucosylated terpene glycoside having a single cellobiosyl residue linked to the terpene glycoside via a b-1,4 glucosidic bond according to some aspects presented herein to the flavored article, in an amount effective to mask the lingering taste of a flavored article.
In some embodiments, the amount effective to confer, enhance, improve, or modify the sweet taste of the flavored article is about 40 ppm, such as from 30 ppm to 50 ppm, or from 20 ppm to 60 ppm, or from 10 ppm to 70 ppm. In some embodiments, the amount effective to confer, enhance, improve, or modify the sweet taste of the flavored article is less than 40 ppm. In some aspects, the amount effective to confer, enhance, improve, or modify the sweet taste of the flavored article is greater than 40 ppm. In some embodiments, the amount effective to confer, enhance, improve, or modify the sweet taste of the flavored article is from 0 and 1000 ppm.
In some aspects, the disclosure provides flavored articles that comprise: the least one glucosylated terpene glycoside (of the foregoing aspects and embodiments); and a foodstuff base, wherein the glucosylated terpene glycoside is selected from the group consisting of: a glucosylated terpene glycoside having a single glucosyl residue linked to the terpene glycoside via a b-1,4 glucosidic bond, and a glucosylated terpene glycoside having a single cellobiosyl residue linked to the terpene glycoside via a b-1,4 glucosidic bond.
Suitable foodstuffs, e.g. foods or beverages are also provided herein. For the purpose of the present disclosure,“foodstuff base” means an edible product, e.g. a food or a beverage. Therefore, a flavored article provided herein comprises the functional formulation, as well as optionally additional benefit agents, corresponding to a desired edible product, e.g., a savory cube, and a flavor effective amount of the least one glucosylated terpene glycoside described herein. In some aspects, the glucosylated terpene glycoside is a glucosylated terpene glycoside having a single glucosyl residue linked to the terpene glycoside via a b-1,4 glucosidic bond. Alternatively, in some aspects, the glucosylated terpene glycoside is a glucosylated terpene glycoside having a single cellobiosyl residue linked to the terpene glycoside via a b-1,4 glucosidic bond.
The compositions and methods provided herein have use in food or beverage products. When the food product is a particulate or powdery food, the dry particles may easily be added thereto by dry-mixing. Typical food products are selected from the group consisting of an instant soup or sauce, a breakfast cereal, a powdered milk, a baby food, a powdered drink, a powdered chocolate drink, a spread, a powdered cereal drink, a chewing gum, an effervescent
tablet, a cereal bar, and a chocolate bar. The powdered foods or drinks may be intended to be consumed after reconstitution of the product with water, milk and/or a juice, or another aqueous liquid.
The food product may be selected from the group consisting of condiments, baked goods, powdery food, bakery filings and fluid dairy products.
Condiments include, without limitation, ketchup, mayonnaise, salad dressing, Worcestershire sauce, fruit-flavored sauce, chocolate sauce, tomato sauce, chili sauce, and mustard.
Baked goods include, without limitation, cakes, cookies, pastries, breads, donuts and the like.
Bakery fillings include, without limitation, low or neutral pH fillings, high, medium or low solids fillings, fruit or milk based (pudding type or mousse type) fillings, hot or cold make-up fillings and nonfat to full-fat fillings.
Fluid dairy products include, without limitation, non-frozen, partially frozen and frozen fluid dairy products such as, for example, milks, ice creams, sorbets and yogurts. Beverage products include, without limitation, carbonated soft drinks, including cola, lemon- lime, root beer, heavy citrus ("dew type"), fruit flavored and cream sodas; powdered soft drinks, as well as liquid concentrates such as fountain syrups and cordials; coffee and coffee - based drinks, coffee substitutes and cereal-based beverages; teas, including dry mix products as well as ready -to-drink teas (herbal and tealeaf based); fruit and vegetable juices and juice flavored beverages as well as juice drinks, nectars, concentrates, punches and "ades";
sweetened and flavored waters, both carbonated and still; sport/energy/health drinks;
alcoholic beverages plus alcohol-free and other low- alcohol products including beer and malt beverages, cider, and wines (still, sparkling, fortified wines and wine coolers); other beverages processed with heating (infusions, pasteurization, ultra-high temperature, ohmic heating or commercial aseptic sterilization) and hot- filled packaging; and cold-filled products made through filtration or other preservation techniques.
The nature and type of the constituents of the foodstuffs or beverages do not warrant a more detailed description here, which in any case would not be exhaustive, the skilled person being able to select them on the basis of his general knowledge and according to the nature of the product.
The proportions in which the least one glucosylated terpene glycoside described herein can be incorporated into the various aforementioned articles or compositions vary within a wide range of values. These values are dependent on the nature of the article to be
flavored and on the desired organoleptic effect as well as the nature of the co-ingredients in a given base when the compounds according to the invention are mixed with flavoring co ingredients, solvents or additives commonly used in the art.
In the case of flavoring compositions, typical concentrations are in the order of about 0.0001 wt% to 1 wt%, or even more, of the least one glucosylated terpene glycoside described herein based on the weight of the consumer product into which they are incorporated. Concentrations lower than these, such as in the order of 0.001 wt% to 0.5 wt% by weight, can be used when the least one glucosylated terpene glycoside described herein are incorporated into flavored articles, percentage being relative to the weight of the article.
EXAMPLES
Example 1: Generation of Mono P-l,4-glucosylated Terpene Glycoside Compounds (Compounds I and II) Using Rubusoside as a Starting Material by a Method According to Some Aspects Presented Herein
Rubusoside (1 g) and cellobiose (1 g) were dissolved in 10 ml NaOAc-HOAc (pH = 5.0, 0.2 M, 5 mL) buffer at room temperature. Subsequently, 200 mg cellulase (Aladdin) was added to the mixture. The mixture containing the enzyme was then heated to 37 °C, and the mixture containing the enzyme was incubated at 37 °C for 24 hours to allow the transglucosidation reaction to proceed, thereby generating the at least one glucosylated terpene glycoside having a single glucosyl residue linked to the terpene glycoside via a b-1,4 glucosidic bond. The reaction was terminated by inactivating the cellulase by incubating the reaction mixture at 100 °C for 30 minutes.
The resulting reaction mixture was analyzed by UPLC-UV, and a mixture containing glucosylated terpene glycosides having a single glucosyl residue linked to the terpene glycoside via a b-1,4 glucosidic bond was identified (See FIG. 1). The identified mixture was purified via a prep-LC. The compounds within the mixture were identified as compounds I and II, at a ratio of 2: 1.
The resulting reaction mixture was analyzed by UPLC-UV, and a mixture containing glucosylated terpene glycosides having a single cellobiosyl residue linked to the terpene glycoside via a b-1,4 glucosidic bond was identified (See FIG. 1). The identified mixture was purified via a prep-LC. The compounds within the mixture were identified as the compound of formula III and the compound of formula IV, at a ratio of 4: 1.
FIG. 2 shows A 1 H NMR spectrum for a composition comprising a mixture of the compound of formula I and the compound of formula II. FIG. 3 shows A 13C NMR spectrum for a composition comprising a mixture of the compound of formula I and the compound of formula II.
Example 2: Sensory Properties of a Composition Comprising Compounds I and II
A composition comprising a mixture of the compound of formula I and the compound of formula II at a ratio (w/w) of 2:1 was generated according to the methods described in Example 1. The composition was dissolved in either a (i) 4% w/w sucrose solution, or (ii) a 0.02% w/w 95% steviol glycoside solution. A panel of 25 trained people evaluated the test solutions for taste properties (sweet, licorice and sweet lingering) on a scale of -5 to 5 (-5 denoted no effect and 5 denoted extremely strong effect, 0 being the intensity of a reference water solution containing either (i) 4% w/w sucrose solution, or (ii) a 0.02% w/w 95% steviol glycoside solution.) The results are shown in the table below.
These data suggest that the composition comprising Compounds I and II at a ratio of 2: 1 significantly enhanced the sweet intensity of the 4% w/w sucrose solution (at 99.9% of confidence level), with and without a nose-clip. The composition comprising the compound of formula I and the compound of formula II at a ratio of 2: 1 significantly decreases the lingering intensity (at 95% confidence level) with nose-clip, and slightly affected the sweet, licorice intensities in the 0.02% SG95 base.
Example 3: Sensory Properties of a Composition Comprising the at Least One Mono P-l,4-glucosylated Terpene Glycosides Presented Herein
A composition comprising the at least one glucosylated terpene glucosides may be generated according to the methods described in Example 1. The composition may be dissolved in either (i) water, or (ii) a 4% w/w sucrose solution, or (iii) 7% (w/w) inverted sugar plus 0.15% citric acid (w/w) solution wherein the final concentration of the
composition in solution may range from 0 to 1000 ppm. Corresponding control solutions of
either (i) 1.5%, or (ii) 4% w/w sucrose, or (iii) 7% (w/w) inverted sugar plus 0.15% citric acid (w/w) solution will also be generated. A panel of 10 experts will evaluate the difference between solution of the test composition and the sucrose solutions, using the 3 -Alternative Forced Choice (3 -AFC) or sweetness intensity scale method. All samples will be tested in blind in a random order.
Claims
1. A compound of formula I:
2. A compound of formula II:
3. A compound of formula III:
4. A compound of formula IV:
5. A method of making a glucosylated terpene glycoside, the method comprising:
(a) providing an aqueous composition comprising a b-glucosyl sugar compound, a terpene glycoside, and a cellulase enzyme; and
(b) reacting the b-glucosyl sugar compound with the terpene glycoside in the presence of the cellulase enzyme to form a glucosylated terpene glycoside having a terpene glycosidyl moiety and one or more b-glucosyl sugar moieties;
wherein the glucosylated terpene glycoside has a b-1,4 glucosidic bond between the terpene glycoside moiety and one of the one or more b-glucosyl sugar moieties.
6. The method of claim 5, further comprising incubating the aqueous composition.
7. The method of claim 5 or 6, wherein the aqueous composition is an aqueous solution.
8. The method of any one of claims 5 to 7, wherein the b-glucosyl sugar compound is cellobiose.
9. The method of any one of claims 5 to 8, wherein the terpene glycoside is stevioside, rebaudioside A, rebaudioside B, rebaudioside C, rebaudioside D, rebaudioside E, rebaudioside F, rebaudioside G, rebaudioside M, dulcoside A, steviolbioside, rubusoside, terpene glycosides found in Stevia rebaudiana Bertoni plants, terpene glycosides found in Rubus suavissimus plants, terpene glycosides found in Siraitis grosvenorii plants, or any mixture thereof.
10. The method of any one of claims 5 to 9, wherein the glucosylated terpene glycoside is mono b-1,4 glucosylated stevioside, mono b-1,4 glucosylated rebaudioside A, mono b-1,4
glucosylated rebaudioside B, mono b-1,4 glucosylated rebaudioside C, mono b-1,4 glucosylated rebaudioside D, mono b-1,4 glucosylated rebaudioside E, mono b-1,4 glucosylated rebaudioside F, mono b-1,4 glucosylated rebaudioside G, mono b-1,4 glucosylated rebaudioside M, mono b-1,4 glucosylated dulcoside A, mono b-1,4 glucosylated steviolbioside, mono b-1,4 glucosylated rubusoside, mono b-1,4 cellobiosylated stevioside, mono b-1,4 cellobiosylated rebaudioside A, mono b-1,4 cellobiosylated rebaudioside B, mono b-1,4 cellobiosylated rebaudioside C, mono b-1,4 cellobiosylated rebaudioside D, mono b-1,4 cellobiosylated rebaudioside E, mono b-1,4 cellobiosylated rebaudioside F, mono b-1,4 cellobiosylated rebaudioside G, mono b-1,4 cellobiosylated rebaudioside M, mono b-1,4 cellobiosylated dulcoside A, mono b-1,4 cellobiosylated steviolbioside, mono b-1,4 cellobiosylated rubusoside, or any mixture thereof.
11. The method of any one of claims 5 to 9, wherein the glucosylated terpene glycoside is the compound of any one of claims 1 to 4.
12. A glucosylated terpene glycoside, which is the glucosylated terpene glycoside formed according to the process of any one of claims 5 to 11.
13. A method of modifying the flavor of a flavored article, the method comprising introducing the glucosylated terpene glycoside of any one of claims 1 to 4 or claim 12 to a flavored composition.
14. The method of claim 13, wherein the method is a method of enhancing a sweet taste of the flavored article.
15. A flavored article, which comprises a carrier and the glucosylated terpene glycoside of any one of claims 1 to 4 or claim 12.
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
CN2018108629 | 2018-09-29 | ||
PCT/EP2019/075782 WO2020064787A1 (en) | 2018-09-29 | 2019-09-25 | Terpene glycoside derivatives and uses thereof |
Publications (1)
Publication Number | Publication Date |
---|---|
EP3774828A1 true EP3774828A1 (en) | 2021-02-17 |
Family
ID=68138027
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
EP19782928.6A Pending EP3774828A1 (en) | 2018-09-29 | 2019-09-25 | Terpene glycoside derivatives and uses thereof |
Country Status (7)
Country | Link |
---|---|
US (1) | US11919920B2 (en) |
EP (1) | EP3774828A1 (en) |
JP (1) | JP2022501308A (en) |
KR (1) | KR20210068321A (en) |
CN (1) | CN112074527A (en) |
BR (1) | BR112020022564A2 (en) |
WO (1) | WO2020064787A1 (en) |
Families Citing this family (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO2017089444A1 (en) * | 2015-11-24 | 2017-06-01 | Firmenich Sa | Glucosylated terpene glycosides |
Family Cites Families (11)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JPS5878562A (en) * | 1981-11-05 | 1983-05-12 | Dainippon Ink & Chem Inc | Improvement of taste of stevia sweetener |
JPS62207292A (en) * | 1986-03-07 | 1987-09-11 | Wakunaga Pharmaceut Co Ltd | Separation of purification of glucoside |
JPH01254696A (en) * | 1988-04-01 | 1989-10-11 | Maruzen Kasei Co Ltd | Novel steviol glycoside and sweetener |
JPH0694473B2 (en) * | 1988-06-20 | 1994-11-24 | 北海道糖業株式会社 | β-glucosyl rubusoside, method for producing the same, and sweetener using the same |
US8257948B1 (en) | 2011-02-17 | 2012-09-04 | Purecircle Usa | Method of preparing alpha-glucosyl Stevia composition |
WO2012153339A2 (en) * | 2011-05-09 | 2012-11-15 | Stevinol Ltd. | Stevia based sweetening composition |
KR20130014227A (en) | 2011-07-29 | 2013-02-07 | 한국생명공학연구원 | NOVEL α-GLUCOSYL STEVIOSIDES AND PROCESS FOR PRODUCING THE SAME |
ES2817049T5 (en) | 2013-06-07 | 2023-11-10 | Purecircle Usa Inc | Stevia extract containing selected steviol glycosides as a taste, flavor and sweetness profile modifier |
EP2954785B1 (en) * | 2014-06-13 | 2018-06-06 | Symrise AG | New composition for improvement of sweet taste comprising rubusoside or alpha-glycolsylrubusoside |
WO2017089444A1 (en) | 2015-11-24 | 2017-06-01 | Firmenich Sa | Glucosylated terpene glycosides |
JP2017123844A (en) * | 2016-01-13 | 2017-07-20 | 独立行政法人国立高等専門学校機構 | Method for producing glycoside |
-
2019
- 2019-09-25 BR BR112020022564-9A patent/BR112020022564A2/en unknown
- 2019-09-25 EP EP19782928.6A patent/EP3774828A1/en active Pending
- 2019-09-25 US US17/252,266 patent/US11919920B2/en active Active
- 2019-09-25 CN CN201980030483.0A patent/CN112074527A/en active Pending
- 2019-09-25 WO PCT/EP2019/075782 patent/WO2020064787A1/en unknown
- 2019-09-25 KR KR1020207031311A patent/KR20210068321A/en active Search and Examination
- 2019-09-25 JP JP2020562165A patent/JP2022501308A/en active Pending
Also Published As
Publication number | Publication date |
---|---|
US11919920B2 (en) | 2024-03-05 |
BR112020022564A2 (en) | 2021-08-24 |
JP2022501308A (en) | 2022-01-06 |
CN112074527A (en) | 2020-12-11 |
KR20210068321A (en) | 2021-06-09 |
WO2020064787A1 (en) | 2020-04-02 |
US20210269469A1 (en) | 2021-09-02 |
Similar Documents
Publication | Publication Date | Title |
---|---|---|
US9609887B2 (en) | Sweetener compositions containing monk fruit extract and rebaudiosides A and B | |
US11896036B2 (en) | Glucosylated terpene glycosides | |
US20220264925A1 (en) | Phloretin | |
WO2018001703A1 (en) | Flavored food and beverage products | |
JP2024056814A (en) | Terpene glycoside derivatives and uses thereof | |
EP3823469B1 (en) | Sweetener formulations and uses | |
US11919920B2 (en) | Terpene glycoside derivatives and uses thereof | |
US20220017563A1 (en) | Mogroside compounds and uses thereof | |
US20210147892A1 (en) | Terpene glycoside derivatives and uses thereof | |
CA3103340A1 (en) | Mouthfeel enhancing composition | |
US20230301330A1 (en) | Flavored Food and Beverage Products |
Legal Events
Date | Code | Title | Description |
---|---|---|---|
STAA | Information on the status of an ep patent application or granted ep patent |
Free format text: STATUS: UNKNOWN |
|
STAA | Information on the status of an ep patent application or granted ep patent |
Free format text: STATUS: THE INTERNATIONAL PUBLICATION HAS BEEN MADE |
|
PUAI | Public reference made under article 153(3) epc to a published international application that has entered the european phase |
Free format text: ORIGINAL CODE: 0009012 |
|
STAA | Information on the status of an ep patent application or granted ep patent |
Free format text: STATUS: REQUEST FOR EXAMINATION WAS MADE |
|
17P | Request for examination filed |
Effective date: 20201029 |
|
AK | Designated contracting states |
Kind code of ref document: A1 Designated state(s): AL AT BE BG CH CY CZ DE DK EE ES FI FR GB GR HR HU IE IS IT LI LT LU LV MC MK MT NL NO PL PT RO RS SE SI SK SM TR |
|
AX | Request for extension of the european patent |
Extension state: BA ME |
|
DAV | Request for validation of the european patent (deleted) | ||
DAX | Request for extension of the european patent (deleted) |